Tag: M.W=100-200

63089-50-9, name is 4-Methylphthalonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C9H6N2

General procedure: A 50 mL round bottom flask equipped with a reflux condenser was charged with the appropriate amount of the substituted phthalonitrile (4.0 mM), zinc triflate (5.0 M%, 0.20 mM), and chlorobenzene (30 mL) under argon. The mixture was stirred to dissolve the phthalonitrile and then 2-aminoalcohol (8.0 mM), dissolved in dry chlorobenzene, was slowly added. The temperature was raised to 135 C and the reaction mixture was refluxed for 24 h. The product of the reaction, which was obtained as an oily residue, was dissolved in 30 mL of dichloromethane and then extracted twice with distilled water (20 mL). The aqueous layer was separated and washed with dichloromethane. The separated organic layers were dried using anhydrous sodium sulfate. The dichloromethane was removed under vacuum on a rotary evaporator to give the crude product, which was then purified using silica gel column chromatography with dichloromethane/ether (4/1) as eluent [14, 16, 17].

The synthetic route of 63089-50-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ibrahim, Mansur B.; Shakil Hussain; Fazal, Atif; Fettouhi, Mohammed; El Ali, Bassam; Journal of Coordination Chemistry; vol. 68; 3; (2015); p. 432 – 448;,
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Reference of 75279-53-7, A common heterocyclic compound, 75279-53-7, name is 4-Chloro-2-fluorobenzeneacetonitrile, molecular formula is C8H5ClFN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Reagents and conditions: (a) EtONa, EtOH, refluxing; (b) CH3NHNH2, HC1, EtOH, IVIW, 100C, 40 mm; (c) 2-(2-isopropyl-1H-benzo[d]imidazol-1-yl)acetic acid,Mukaiyama?s reagent, TEA, DCM, THF, MW, 75C, 30 mm. A mixture of 1.8 ml (15mmol) of ethyl 2,2,2-trifluoroacetate (ib) and 1.2 g (7.1 mmol) of 2-(4-chloro-2-fluorophenyl)acetonitrile (la) in 10 ml of ethanol was slowly dropped into hot solutionof 1.2 g of sodium in 20 ml of ethanol. The mixture was refluxed overnight. Thesolution turns red. After cooled down, the solution was poured into 250 ml of cold wateracidified with 10 ml concentrated HC1. The mixture was extracted with ethyl acetate.The ethyl acetate extraction was washed with water, brine and dried over MgSO4. Ethylacetate was removed and the residual reddish oil of 2-(4-chloro-2-fluorophenyl)-4,4,4-trifluoro-3-oxobutanenitrile (ic) was obtained in 1.2 g. The raw material was dissolvedin 10 ml of ethanol and used in next step without further purification. A mixture of 2 mlof the above ethanol solution and 72 tl of methylhydrazine with 0.14 ml ofconcentrated HC1 was irradiated in microwave oven at 100C for 40mm. The solutionwas treated with saturated NaHCO3 and extracted by ethyl acetate. The organic layerwas washed with water, brine, dried over MgSO4 and concentrated. The yellow residuewas subjected to flash chromatography purification with MeOHIDCM to give 120 mgof 4-(4-chloro-2-fluorophenyl)-3 -(trifluoromethyl)- 1-methyl-i H-pyrazol-5 -amine (id)as light yellow solid. M/Z = 294.6 (M+i). To a mixture of 2-(2-isopropyl-1H-benzo[d]imidazol-i-yl)acetic acid (0.16 mmol, from ChemBridge) and Mukaiyama?sreagent (0.38 mmol) in 1.5 ml anhydrous DCM, 4-(4-chloro-2-fluorophenyl)-3-(trifluoromethyl)- i-methyl-i H-pyrazol-5 -amine (1 d, 0.12 mmol) obtained as described above, triethylamine (0.40 mmol) and 0.5 ml of anhydrous THF were added. The mixture was vortexed and subject to microwave irradiation for 30 mm at 75C to give a deep green clear solution. Then 80 ml of ethyl acetate was added and washed with 80 ml of saturated NaHCO3 twice, brine and dried over MgSO4. After solvent removal andpurification on a flash chromatography, slightly brown color solid was obtained. After recrystallization in ethyl acetate/hexane, 45 mg of Compound (1) was given as white powder solid. ?HNMR (500 MFIz, MeOD) 7.79 (d, J = 7.7 Hz, 1H), 7.62 (dt, J = 15.8, 8.2 Hz, 3H), 7.36 – 7.15 (m, 3H), 5.55 (s, 2H), 3.89 (s, 3H), 3.55 – 3.44 (m, 1H), 1.47 (d, J = 6.9 Hz, 6H); M/Z =494.9 (M+1).

The synthetic route of 75279-53-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MMV MEDICINES FOR MALARIA VENTURE; DREXEL UNIVERSITY; UNIVERSITY OF WASHINGTON; BURROWS, Jeremy; WYVRATT, Matthew; VAIDYA, Akhil; KORTAGERE, Sandhya; FAN, Erkang; CHATTERJEE, Arnab Kumar; NAGLE, Advait Suresh; KATO, Tomoyo; WO2015/8246; (2015); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 455-18-5, name is 4-(Trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H4F3N

Reaction Scheme 3, Step 1 4-Trifluoromethylphenyl-amidoxime A solution of 4-trifluoromethyl benzonitrile (Avocado 14514, 15 g) in toluene (200 ml) was treated with methanol (15 ml) followed by hydroxylamine hydrochloride (2.25 g) and potassium tert-butoxide (3.52 g). The mixture was heated to 80 C. and treated with further portions of hydroxylamine hydrochloride (1.07 g) and potassium tert-butoxide (3.52 g) after 2, 4 and 6 h. The mixture was stirred for 16 h, and then cooled. The solvents were evaporated and the residue partitioned between water (100 ml) and dichloromethane (200 ml). The aqueous layer was extracted with two further portions of dichloromethane (2*200 ml). The organic solutions were combined, dried (anhydrous magnesium sulphate), filtered and evaporated to give the title compound as a white solid (16.7 g, 93%). Mass spectrum, 215 [M+H]+.

The synthetic route of 455-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Edlin, Christopher David; Redshaw, Sally; Smith, Ian Edward David; Walter, Daryl Simon; US2003/69276; (2003); A1;,
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Synthetic Route of 623-03-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 623-03-0 as follows.

Under a nitrogen atmosphere, a reaction vessel of 20 ml in volume was charged with bis(pinacolate)diboron (1.1 Ig (4.4 mmol)), degassed methanol (7.2 g) and diisopropylethylamine (1.13 g (8.7 mmol)) and stirred at room temperature. The reaction vessel was charged with bis(l,5-cyclooctadiene)nickel (32 mg (0.12 mmol)), triphenylphosphine (61 mg (0.23 mmol)), and 4-chlorobenzonitrile (0.40 g (2.9 mmol)) and stirred at 3O0C for 21 hours, and thereafter stirred at 500C for 3 hours. The reaction solution was analyzed by gas chromatography. As a result, 4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)benzonitrile was contained in an amount of 0.58 g(2.6 mmol, yield: 88%).

According to the analysis of related databases, 623-03-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; GENENTECH, INC.; MIKI, Takashi; SHIMASAKI, Yasuharu; BABU, Srinivasan; CHENG, Zhigang; REYNOLDS, Mark, E.; TIAN, Qingping; WO2010/110782; (2010); A1;,
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Synthetic Route of 915394-28-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 915394-28-4, name is 2-Methyl-2-(3-nitrophenyl)propanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-Methyl-2-(3-nitrophenyl)propanenitrile (0.6 g, 3.15 mmol) obtained in Step (1) above was stirred in a solvent of methanol. The reaction solution was mixed with Pd/C (0.06 g, 0.56 mmol), followed by stirring under hydrogen conditions for about 2 hours at room temperature. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with methanol. The filtrate was concentrated under reduced pressure to obtain the title compound (0.48 g, 95%). 1H-NMR Spectrum (300 MHz, DMSO-d6): delta 7.06 (t, 1H), 6.71 (s, 1H), 6.61 (d, 1H), 6.52 (d, 1H), 5.21 (s, 2H), 1.61 (s, 6H). MS (ESI+, m/z): 161 [M+H]+

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Methyl-2-(3-nitrophenyl)propanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HANMI PHARM. CO., LTD.; Bae, In Hwan; Han, Sang Mi; Kwak, Eun Joo; Ahn, Young Gil; Suh, Kwee Hyun; US2015/191450; (2015); A1;,
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606080-43-7, name is Methyl 2-cyano-5-fluorobenzoate, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: nitriles-buliding-blocks

b) Synthesis of 2-Cyano-5-dimethylamino-benzoic acid methyl ester (21b). To a stirred solution of 4.03 g (22,5 mmol) 21a and 60.0 ml dimethylsulphoxid are added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture is stirred for 15h at 65C in an autoclave and is reduced with high vacuum rotation evaporator at 65C. The residue is diluted with dichloromethane, washed twice with water. The combined water phases are extracted with dichloromethane. The combined dichloromethane phases are washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude is purified by column chromatography and the desired product 21b is obtained in 89.0 % yield (4.09 g, 20.0 mmol). MS-ESI: 205 (M+ +1, 100),

The synthetic route of 606080-43-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1897885; (2008); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 766-84-7, name is 3-Chlorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H4ClN

Preparation of N-(4-chloro-2-cyclohexanecarbonylphenyl)trifluoromethanesulfonamide (Formula 29E). a) To a stirred solution of 3-chlorobenzonitrile (2.0 g, 14.54 mmol) and cyclohexylmagnesium chloride (2M in Et2O) (8.0 mL, 15.99 mmol) in THF (20 mL) was added CuCl (29 mg, 0.29 mmol), and the mixture was refluxed for 30 minutes. After cooling to RT, cold 1N HCl (10 mL) was added cautiously, the THF removed under reduced pressure, further 1N HCl (30 mL) added and the reaction heated at 90 C. for 1 hour. To the cooled reaction mixture was added water (20 mL) and CH2Cl2 (50 mL), the phases separated, and the aqueous phase again extracted with CH2Cl2. The combined organics were washed with water, dried over MgSO4 and the solvent evaporated under vacuum. The residue was filtered through a pad of silica (eluting with CH2Cl2) to afford (3-chlorophenyl)cyclohexylmethanone 26E (3.14 g, 97%), as a yellow liquid.

The synthetic route of 766-84-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Meyer, Adam Gerhard; Winzenberg, Kevin Norman; Sawutz, David G.; Liepa, Andris Juris; US2006/63841; (2006); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 4210-32-6 as follows. HPLC of Formula: C11H13N

3-(4-(1,1-Dimethylethyl)phenyl)-5-methylisoquinolin-1-one (99h). Butyllithium (2.5 M in hexanes, 0.46 mL, 1.14 mmol) was added to dry diisopropylamine (127.5 mg, 1.3 mmol) in dry tetrahydrofuran (2.0 mL) at -78¡ãC and the mixture was stirred at -78¡ãC for 10 min. 2,3,N,N-Tetramethylbenzamide 16 (200 mg, 1.1 mmol) in dry tetrahydrofuran (2.0 mL) was added and the mixture was stirred for 1 h at -78¡ãC. 4-(1 ,1-Dimethylethyl)- benzonitrile (available from Sigma-Aldrich – catalogue number 527785) (180 mg, 1.1 mmol) in dry tetrahydrofuran (2.0 mL) was added and the mixture was stirred for 1 h at -78¡ãC, then at 20¡ãC for 16 h. Water (1.0 mL) was added. The mixture was diluted with dichloromethane. This mixture was washed thrice with brine and dried. The solvent was evaporated and the residue was washed (EtOH) to give 3-(4-(1 ,1-dimethylethyl)- phenyl)-5-methylisoquinolin-1-one 99h (96.5 mg, 29percent) as a white solid: mp 204-206¡ãC; IR vmax3295, 1642 cm”1; 1H NMR ((CD3)2SO) (COSY) delta 1.33 (9 H, s, CMe3), 2.55 (3 H, s, 5-Me), 6.82 (1 H, s, 4-H), 7.35 (1 H, t, J = 7.6 Hz, 7-H), 7.51 (2 H, d, J = 7.6 Hz, Ph 3,5-H2), 7.54 (1 H, d, J = 7.2 Hz, 6-H), 7.75 (2 H, d, J = 7.6 Hz, Ph 2,6-H2), 8.06 (1 H, d, J = 8.0 Hz, 8-H), 1 1.48 (1 H, br, NH); 13C NMR ((CD3)2SO) (HSQC / HMBC) delta 18.75 (Me), 30.97 (CMe3), 34.44 (CMe3), 99.60 (4-C), 124.56 (8-C), 124.86 (8a-C), 125.51 (Ph 3,5-C2), 125.72 (7-C), 126.56 (Ph 2,6-C2), 131.44 (Ph 1-C), 133.15 (6-C), 133.60 (4a-C), 136.69 (5-C), 139.84 (3-C), 151.87 (Ph 4-C), 162.97 (1-C); MS m/z 292.1686 (M + H)+ (C20H22NO requires 292.1703).

According to the analysis of related databases, 4210-32-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF BATH; THREADGILL, Michael David; LLOYD, Matthew David; THOMPSON, Andrew Spencer; NATHUBHAI, Amit; WOOD, Pauline Joy; PAINE, Helen Angharad; KUMPAN, Ekaterina; SUNDERLAND, Peter Thomas; CHUE YEN WOON, Esther; WO2014/87165; (2014); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6574-99-8, name is 3,4-Dichlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C7H3Cl2N

To the reaction vessel of the dry strip rectification column, 350 g of N-methylpyrrolidone (NMP) and anhydrous potassium fluoride (230 g, 3.96 mol) were placed.Add 150g of toluene and reflux to separate water for about 2 hours. After the end of water separation, the toluene is distilled out and recycled for the next application., 3,4-dichlorobenzonitrile (200 g, 1.16 mol), bis-(N,N’-1,3-dimethyl-2-imidazolidinyl)-ammonium chloride (10 g, 0.04 mol) ),Sodium lauryl sulfate (5 g) and sodium thiosulfate (10 g) were heated to 200-210 C for 4 hours.The rectification column received 157 g of a crude product of 3,4-difluorobenzonitrile, and the crude product was subjected to secondary rectification to obtain 146 g of a 3,4-difluorobenzonitrile product having a purity of 99% and a molar yield of 90.7%..

The synthetic route of 6574-99-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Feng Shan Group Co., Ltd.; Chen Baoming; Wang Jinyang; Zhang Qingbao; Ma Tiantian; Dou Feiyang; Yao Jinli; Li Xing; Li Junqing; Wang Bo; Shan Yongxiang; Yin Ping; Yin Fengshan; (8 pag.)CN108409605; (2018); A;,
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Reference of 64113-84-4,Some common heterocyclic compound, 64113-84-4, name is 2-Fluoro-5-methylbenzonitrile, molecular formula is C8H6FN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

a 4-fluoro-3-cyanobenzoic acid To a mixture of 2-fluoro-5-methylbenzonitrile (13.5 g, 0.1 mol), tetrabutylammonium bromide (1.61 g, 5 mmol), and ruthenium(III)chloride trihydrate (0.261 g, 1 mmol) in dichloromethane (150 mL) was added a solution of sodium hypochlorite (645 mL, 0.45 mol) which had been neutralized to pH 9 with 20% sulfuric acid. The reaction mixture was stirred and maintained at pH 9 by adding 20% sodium hydroxide solution at RT. After 3 h, the aqueous phase was separated and neutralized to pH 2 with 20% sulfuric acid and the solid which formed was filtered to give the title compound (3.4 g, 20%). mp 177-8 C. 1 H NMR (CDCl3) delta 7.35 (t, J=8.70 Hz, 1H), 8.38 (m, 1H), 8.42 (m, 1H).

The synthetic route of 64113-84-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham Corporation; US6117866; (2000); A;,
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