Tag: M.W=100-200

These common heterocyclic compound, 218632-01-0, name is 3-Fluoro-4-nitrobenzonitrile, 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. Computed Properties of C7H3FN2O2

Example 7; (5-Cvano-2-nitro-phenyl)-(5-morpholin-4-ylmethyl-pyridin-2-yl)-acetic acid ethyl ester using 3-fluoro-4-nitrobenzonitrile in tetrahydrofuran and toluene; To a solution of (5-Morpholin-4-ylmethyl-pyridin-2-yl)-acetic acid ethyl ester (51.03g, 74.5% w/w%, 143.8mmol; Example 5) in toluene (204.1ml) was added a solution of 3- fluoro-4-nitrobenzonitrile (24.5 g, 151mmol) in tetrahydrofuran (357ml) and the solution was degassed three times with nitrogen and then cooled to -200C. Lithium tert-butoxide solution in tetrahydrofuran (137.ml, 20w/w%, 302mmol) was added dropwise over lhr. After stirring for an additional lhr 20min the reaction mixture was then added to a cold aqueous solution of ammonium chloride (188ml, 4.58M, 6862.7mmol) at 00C. The biphasic mixture was warmed to 300C and Celite (76.5g) added, then filtered. The filter cake was washed twice with toluene (153ml) then the combined filtrate was separated and the organic layer washed twice with water (153ml). The organic layer was concentrated by distillation to give (5-Cyano-2-nitro-phenyl)-(5-morpholin-4-ylmethyl-pyridin-2-yl)-acetic acid ethyl ester as a toluene solution (196ml) (titration, HCIO4, assay 80.47 w/w%) .The crude product mixture is directly used in the next step.

The synthetic route of 3-Fluoro-4-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2008/130312; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6575-11-7, name is 2-Amino-6-chlorobenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6575-11-7, Computed Properties of C7H5ClN2

A mixture of 2-amino-6-chlorobenzonitrile (17.72 g, 0.116 mol) and tetrahydro-2,5- dimethoxyfuran (0.116 mol) in HO Ac (100 ml) was stirred and re fluxed for 30 min. Subsequently, the mixture was cooled and evaporated. The residue was purified over silica gel on a glass filter (eluent: DCM). The product fractions were collected and the solvent was evaporated. The residue was crystallized from EtOH. Yield: 18.83 g of intermediate 3 (80 % yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-6-chlorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; MEERPOEL, Lieven; MAES, Louis, Jules, Roger, Marie; DE WIT, Kelly; AUGUSTYNS, Koen, Jan, Ludovicus; WO2012/150305; (2012); 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 71825-51-9 as follows. Recommanded Product: 71825-51-9

2-Methyl-2-(4-nitrophenyl)propanenitrile (Compound of step 1, 16 g, 84.1 mmol) and Raney- Ni (4.16 g) were shaken in THF-MeOH [(1:1), 160 mL] under 40 psi of hydrogen for 10 hours at RT, After completion of reaction, the catalyst was filtered-off and the solvent was evaporated to dryness. The crude product was purified by column chromatography (silica gel, ethyl acetate in hexane) to obtain the title compound as oil.Yield: 10 g (74 %); 1H NMR (DMSO-d6, 300 MHz): delta 7.091-7.119 (d, 2H, J= 8.4Hz), 6.533- 6.561 (d, 2H, J= 8.4Hz), 5.135 (s, 2H), 1.568 (s, 6H); MS: m/z 161 (M+).

According to the analysis of related databases, 71825-51-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PIRAMAL LIFE SCIENCES LIMITED; KUMAR, Sanjay; VISHWAKARMA, Ram; MUNDADA, Ramswaroop; DEORE, Vijaykumar; KUMAR, Pramod; SHARMA, Somesh; WO2011/1212; (2011); A1;,
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Reference of 243128-37-2, 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. 243128-37-2, name is 4-Fluoro-3-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4.1.1. Synthesis of the Compounds 4 from Scheme 1 (Benzonitrile Derivatives)Synthesis of 4-morpholino-3-methoxy-benzonitrile (4.3) (for Examples 10, 70)6.7 mL (75 mmol) morpholine was stirred into 50 ml dimethylsulphoxide together with 20 g (141 mmol) potassium carbonate and 10.0 g (66 mmol) 4-fluoro-3-methoxy-benzonitrile for 8 h at 100 C. 500 ml ice water was added to the reaction mixture and the precipitate formed was filtered off and dried.Yield: 11.2 g (51 mmol=78% of theory)Analysis: HPLC-MS (method D): Rt: 1.36 min, (M+H)+: 219

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, 4-Fluoro-3-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/201608; (2011); A1;,
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Electric Literature of 53312-82-6, 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. 53312-82-6, name is 4-Amino-2-bromobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-amino-2-bromobenzonitrile (440 mg, 2.2 mmol), ferf-butyl 2-oxo-6azaspiro[3.4]octane-6-carboxylate (495 mg, 2.2 mmol) and decaborane (43 mg, 0.35 mmol) in MeOH (20 mL) was stirred at 50 C overnight under Ar. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Petroleum ether/EtOAc = 3/1) to afford intermediate 39 (406 mg, 45% yield) as a white solid.

The synthetic route of 4-Amino-2-bromobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); A1;,
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Related Products of 117482-84-5, 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. 117482-84-5, name is 3-Chloro-4-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 84B 3-chloro-4-(methylamino)benzonitrile A mixture of 3-chloro-4-fluorobenzonitrile (5.2 g, 33 mmol), THF (55 mL), and 40% methylamine in water (25 mL, 290 mmol) in a sealed tube was heated to 65 C. for 1.5 hours, cooled to room temperature. The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated. The resulting solid was dried for about 16 hours under high vacuum in the presence of P2O5 to provide 6.3 g (95%) of the desired product. MS (DCI/NH3) m/z 184, 186 (M+H+NH3)+; 1H NMR (DMSO-d6) delta 7.72 (d, 1H), 7.55 (dd, 1H), 6.70 (d, 1H), 6.52 (br q, 1H), 2.80 (d, 3H).

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, 3-Chloro-4-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Claiborne, Akiyo K.; Gwaltney, II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2002/115640; (2002); A1;,
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Adding a certain compound to certain chemical reactions, such as: 94087-40-8, name is 3-Chloro-2-fluorobenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 94087-40-8, name: 3-Chloro-2-fluorobenzonitrile

To a solution of 11 (3.57 g, 16.9 mmol, 1 eq) and 3-chloro-2-fluorobenzonitrile (5.25 g, 33.74 mol, 2 eq) in dry DMSO (125 mL) was added K2CO3 (7 g, 50.6 mmol, 3.1 eq). The reaction mixture was stirred at rt for 24 h and partitioned between EtOAc and brine. The aqueous phase was extracted with EtOAc and the combined EtOAc extracts were washed with brine, dried over Na2SO4, and evaporated. Chromatography on a silica column with eluent of 20:1 CH2Cl2:Me0H afforded (R)-3-chloro-2-[2-chloro-5-(5-oxo-pyrrolidin-3-yl> phenoxy]-benzonitrile, 12. 2.4 Results[0172] Analytical data for structure 9 is provided below.2.4a (R)-3-chloro-2-[2-chloro-5-(5-oxo-pyrrolidin-3-yl)’phenoxy]-benzonit}”ile [0173] MS m/z 347.0 (M + 1).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; IRM LLC; WO2006/81554; (2006); A2;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H7NO

EXAMPLE 34 This example illustrates the preparation of compound 34. 4-Hydroxymethyl-benzonitrile (3.1 g, 23.3 mmoles) was combined with N,N-diisopropylethylamine (4.9 mL, 28 mmoles) in 100 mL of anhydrous THF. To this solution was added MOMCl (3.5 mL, 46.1 mmoles) and the mixture was stirred at room temperature for 16 hours. After this period a solution of NH4OH/H2O (1:1, 20 mL) was added (-MOMCl) and the solution was stirred for 15 minutes. After this period the reaction mixture was evaporated in vacuo (-THF) and the resulting mixture was extracted with DCM (3*30 mL). The combined DCM layer was dried over anhydrous Na2SO4, evaporated in vacuo, and the resulting crude product was purified using flash silica chromatography (0-20% EtOAc/Hexane) to yield 1.6 g (39% yield) of 4-Methoxymethoxymethylbenzonitrile as a colorless liquid.

According to the analysis of related databases, 874-89-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayne, Christopher D.; Johnson, Alan T.; Lu, Shao-Po; Mohan, Raju; Griffith, Ronald C.; US2003/181420; (2003); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 19472-74-3, name is 2-Bromophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H6BrN

2-Bromophenylacetonitrile (20.0 g, 0.1 mol) was dissolved in THF (100 mL), iced water,1 M borane tetrahydrofuran solution (200 mL, 0.2 mol) was added dropwise, and the mixture was dropped.Slowly warm to 80 C, stir for 24 h, place the cooled ice bath after cooling.Methanol (50 mL), 3N hydrochloric acid (30 mL) were slowly added dropwise, and the temperature was raised to 80 C.Stir for 4 h, concentrate and dilute with water (100 mL) and wash with diethyl ether (50 mL×2).The aqueous phase is adjusted to pH=10 with saturated sodium carbonate solution.Extracted with EA (50 mL×2), dried and concentrated.17.4 g (85.2%) of a pale yellow oily liquid was obtained.

According to the analysis of related databases, 19472-74-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Liu Zhanzhu; Shen Zhufang; Sun Zhaozhu; Pan Xuan; Zhou Tian; Huan Yi; Guan Baohe; (76 pag.)CN110294744; (2019); A;,
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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. 123-06-8, name is Ethoxymethylenemalononitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethoxymethylenemalononitrile

To 2-(ethoxymethylene)propanedinitrile (20 g, 163.80 mmol) was added hydrazine hydrate (15.9 mL, 327.60 mmol) dropwise at 0 C and the resultant reaction mixture was heated at 100 C in a closed reagent bottle for 1 h. The reaction was monitored by TLC. After completion of reaction, the mixture was cooled to RT and water (50 mL) was added to the reaction mixture. The product was extracted using EtOAc (3×200 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 15 g of 5-amino-1H-pyrazole-4-carbonitrile as a light brown solid.

The synthetic route of 123-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; CHAKRAVARTY, Sarvajit; GREEN, Michael, John; PHAM, Son, Minh; PUJALA, Brahmam; AGARWAL, Anil, Kumar; NAYAK, Ajan, Kumar; KHARE, Sweta; GUGULOTH, Rambabu; RANDIVE, Nitin, Atmaram; WO2015/58084; (2015); A1;,
Nitrile – Wikipedia,
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