Category: nitriles-buliding-blocks

Electric Literature of 914637-31-3,Some common heterocyclic compound, 914637-31-3, name is 2-(3-Fluoro-5-methoxyphenyl)acetonitrile, molecular formula is C9H8FNO, 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.

To a solution of 2-(3-fluoro-5-methoxyphenyl)acetonitrile (2.62 g, 16 mmol) in MeOH:H20 (1 :1; 15 mL), NaOH (1.28 g, 32 mmol) was added. Then the mixture was stirred at 65 C for 4 h. The mixture was cooled to room temperature, and 4M aqueous HCl solution was added until the pH was adjusted to 4~5. The mixture was filtered and the solid obtained was washed with H20 (2 x 5 mL) to give 2.33 g of 2-(3-fluoro-5-methoxyphenyl)acetic acid. H NMR (CDC13): delta 6.52-6.62 (m, 3H), 3.78 (s, 3H), 3.59 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3-Fluoro-5-methoxyphenyl)acetonitrile, its application will become more common.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; KAHRAMAN, Mehmet; GOVEK, Steven, P.; NAGASAWA, Johnny, Y.; SMITH, Nicholas, D.; WO2011/156518; (2011); A2;,
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Application of 42872-73-1, 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. 42872-73-1, name is 2-Bromo-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of Int4.1 (500 mg) in toluene (7.5 ml) was added 2-bromo-4-methylbenzonitrile (1.2 g), Pd2dba3 (140 mg) and rac-BINAP (191 mg). The flask was twice degased and backfilled with argon. The mixture was stirred at r.t. for 5 minutes. Caesium carbonate (2.5 g) was added, the flask was twice degased and backfilled with argon and the mixture was heated to reflux for 4h. Further Pd2dba3 (140 mg) and rac-BINAP (191 mg) was added, the flask was twice degased and backfilled with argon and the mixture was heated to reflux for 2h. Water was added and the reaction mixture was extracted with a mixture of dichloromethane and methanol (10:1). The combined organic phases were washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 205 mg of the title compound. 1H-NMR (400MHz, DMSO-d6): delta [ppm]= 1.46 (s, 9H), 2.35 (s, 3H), 6.96 (dd, 1H), 7.54 (d, 2H), 7.57 – 7.63 (m, 2H), 7.66 (d, 2H), 7.79 (s, 1 H), 7.87 (dd, 1 H), 9.04 (dd, 1 H), 9.34 (s, 1 H), 9.47 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-4-methylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bayer Schering Pharma AG; EP2343295; (2011); A1;,
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Application of 19472-74-3, 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. 19472-74-3, name is 2-Bromophenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(2-Methylpyridin-3-yl)boronic acid (550 mg, 3.2 mmol), 2-(2-bromophenyl)acetonitrile (597 mg, 3.05 mmol), Pd(PPh3)4 (176 mg, 0.15 mmol) and K2C03 (176 mg, 0.15 mmol) were dissolved in /’PrOH (5 mL) and water (2 mL) and the mixture was heated at 80 C under N2 for 5h. The mixture was filtered and the solid was washed with DCM (20 mL). The filtrate was washed with brine, dried over sodium sulfate and concentrated. Column chromatography (DCM/MeOH = 100:0 – 20:1) gave the product (300 mg, 45% yield) as a yellow solid. LCMS (ES-API): Rt 0.44 min; m/z 209.1 [M+H]+.

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

Reference:
Patent; CTXT PTY LIMITED; MORROW, Benjamin Joseph; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; LAGIAKOS, Helen Rachel; WALKER, Scott Raymond; BOZIKIS, Ylva Elisabet Bergman; STEVENSON, Graeme Irvine; CUZZUPE, Anthony Nicholas; STUPPLE, Paul Anthony; (313 pag.)WO2019/43139; (2019); A1;,
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Application of 628-20-6, 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. 628-20-6, name is 4-Chlorobutyronitrile, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 1 Preparation of cyclopropylnitrile (2 molar scale) STR2 A stirred mixture of 4-chlorobutyronitrile (213.4 g, 2.0 mole), sodium chloride (58.0 g, 0.5 mole) and 2.0 g of water in 200 g of dimethylsulfoxide is heated to 80 C., treated with ground solid sodium hydroxide (88 g, 2.2 mole) over a 3 hour period and held at 80 C. for about 1 additional hour. The reaction mixture is cooled to room temperature neutralized to about pH6.8 with concentrated HCl (37% aqueous solution), diluted with 200 ml water (readjusted pH to 6.8 with 37% HCl) and azeotropically distilled with a Dean Stark trap to remove the cyclopropylnitrile/water azeotrope. The aqueous layer is continuously returned to the distillation pot to give the initial product as the distillate cyclopropylnitrile, 133.5 g. A 121.5 g sample of this cyclopropylnitrile is azeotropically distilled using a Dean Stark trap (to remove water) and continuous return of the organic layer to give the final productproduct cyclopropylnitrile, 106.6. g, 87.8% yield, 98% pure by GLC analysis and 0.04% H2 O by Karl Fischer titration.

The chemical industry reduces the impact on the environment during synthesis 4-Chlorobutyronitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; American Cyanamid Company; US5380911; (1995); A;,
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Related Products of 58633-04-8, These common heterocyclic compound, 58633-04-8, name is 4-Amino-3,5-dibromobenzonitrile, 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.

EXAMPLE 26 PREPARATION OF 3,5-DIBROMOBENZONITRILE STR38 To a stirred solution of t-butylnitrite (53.5 muL, 0.449 mmoles) in 1 ml sieve dried dimethylformamide at 50 C. under an atmosphere of nitrogen was added a solution of 4-amino-3,5-dibromobenzonitrile (50 mg, 0.179 mmoles) in 1 mL of DMF. The mixture was stirred at 50 C. for 0.5 hour and partitioned between diethyl ether, ice-water, and ammonium chloride. The organic phase was separated, washed with water and brine, dried over anhydrous sodium, filtered, and evaporated. Purification by plate layer chromatography using hexane-ethyl acetate (9:1) as the eluant provided 28 mg (59%) of white, crystalline product. NMR (CDCl3) delta:7.7 (d, J=1.8Hz, 2H), 7.9 (t, J=1.8Hz, 1H).

Statistics shows that 4-Amino-3,5-dibromobenzonitrile is playing an increasingly important role. we look forward to future research findings about 58633-04-8.

Reference:
Patent; Merck & Co. Inc.; US5455239; (1995); A;,
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Adding a certain compound to certain chemical reactions, such as: 14533-86-9, name is Methyl (E)-2-Cyano-3-phenylacrylate, 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 14533-86-9, name: Methyl (E)-2-Cyano-3-phenylacrylate

(E)-methyl-2-cyano-3-phenylacrylate 30a (1.40 g, 7.48mmol, 1.0 equiv) and zinc powder (7.83 g, 119.7 mmol,16.0 equiv) were dissolved in 50 mL glacial acetic acid and the solution was stirred for 2.5 h at 100 C. The reaction mixture was filtered through a celite pad and washed with 100 mL EtOAc. The filtrate was neutralised with aq. NaHCO3 solution and the organic layer was separated,washed with brine (2 ¡Á 25 mL), dried over Na2SO4 and the solvent removed under reduced pressure. The crude product was further purified on a silica column with a solvent mixture of 1:9 (EtOAc/hexane) with the desired nitrile isolated as a colourless oil. 6 Isolated yield: 0.583 g (41%, 7.48 mmol),

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, Methyl (E)-2-Cyano-3-phenylacrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mallia, Carl J.; Englert, Lukas; Walter, Gary C.; Baxendale, Ian R.; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 875 – 883;,
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Related Products of 2469-99-0, These common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, 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.

Step B: 5-Methyl-2-phenyl-2H-pyrazol-3-ylamine Into a 1000-mL 3-necked round bottom flask, was placed a solution of 3-oxobutanenitrile (23 g, 277.11 mmol, 1.00 equiv) in ethanol (400 mL), 1-phenylhydrazine (30 g, 277.78 mmol, 1.00 equiv). The resulting solution was heated to reflux overnight in an oil bath. The resulting mixture was then concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10-1:5) to yield 3-methyl-1-phenyl-1H-pyrazol-5-amine as a yellow solid.

The synthetic route of 2469-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHANG, Xuqing; ABAD, Marta G.; GIBBS, Alan C.; KUO, Gee-Hong; KUO, Lawrence C.; SONG, Fengbin; SUI, Zhihua; US2011/263559; (2011); A1;,
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455-18-5, name is 4-(Trifluoromethyl)benzonitrile, 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

General procedure: To the solution of NaOH (5.93 g, 0.15 mol) in water (20 mL) and ethanol (120 mL), hydroxylamine hydrochloride (10.33 g, 0.15 mol) was added in one portion at room temperature. The resulting mixture was then stirred for 10 min, followed by the addition of 4-substituted cyanobenzene (1, 0.12 mol) and then heated to reflux for 4 h. After cooled to room temperature, the reaction mixture was evaporated in vacuo to remove ethanol. The obtained slurry was dissolved in ethyl acetate and filtered. The filtrate was collected, dried over anhydrous Na2SO4, and then concentrated to give corresponding compound 2, which was used in next step without any purification.

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

Reference:
Article; Dai, Hong; Chen, Jia; Li, Gang; Ge, Shushan; Shi, Yujun; Fang, Yuan; Ling, Yong; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 950 – 953;,
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Some common heterocyclic compound, 17626-40-3, name is 3,4-Diaminobenzonitrile, molecular formula is C7H7N3, 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. Recommanded Product: 17626-40-3

Intermediate 44: (Trans)-N-(2-amino-5-cvanophenyl)-2-oxo-3-(2-pyridinyl)-1-oxa-3- azaspiro[4.51decane-8-carboxamide; To a shaken mixture of (trans)-2-oxo-3-(2-pyridinyl)-1-oxa-3-azaspiro[4.5]decane-8- carboxylic acid (Intermediate 45, 1 10 mg, 0.398 mmol) and 3,4-diaminobenzonitrile (commercially available, 80 mg, 0.597 mmol) in anhydrous pyridine (1.6 ml) was added EDCHCI (153 mg, 0.796 mmol) and the reaction mixture was shaken at room temperature for 1 hour. The mixture was concentrated under vacuum and the residue was partitioned between saturated sodium bicarbonate solution and EtOAc (2×10 ml). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated under vacuum to give a residue which was purified by silica gel chromatography eluting with 40% Et2ODCM, Et2O 100% then 10% MeOHDCM to afford the title compound as solid (155 mg, 85%). 1 H-NMR (400 MHz, DMSO-d6): delta 1.59-1.79 (m, 4H), 1.93-2.02 (m, 2H), 2.03-2.10 (m, 2H), 4.03-4.07 (s, 2H), 5.92 (br s., 2H), 6.77 (d, 1 H), 7.13-7.18 (m, 1 H), 7.29 (d, 1 H), 7.62 (s, 1 H), 7.82-7.88 (m, 1 H), 8.1 1 (d, 1 H), 8.39 (d, 1 H), 9.09-9.16 (s, 1 H); UPLC-MS: 0.60 min, m/z 392 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17626-40-3, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/129007; (2008); A1;,
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Synthetic Route of 874-89-5, These common heterocyclic compound, 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, 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.

Preparation of Intermediate 2 (Int.2); N’-Hydroxy-4-(hydroxymethyl)benzimidamide; [00110] A solution of 4-(hydroxymethyl)benzonitrile (22.43g, 0.1685g), hydroxylamine hydrochloride (18.67g, 0.2689 mol) and NaHCO3 (45.22g, 0.538 mol) in methanol (250 mL) was heated to reflux overnight. Upon cooling, the heterogeneous mixture was filtered and the solids were washed with additional methanol. The filtrate was evaporated to dryness to afford an off-white solid. The solids were suspended in ~75 mL hot methanol, then cooled to room temperature and filtered. The filtrate was evaporated to afford N’-hydroxy-4- (hydroxymethyl)benzimidamide (28.5g) as a white solid. The material was used without further purification. The compound had an HPLC retention time = 0.232 min. – Column: CHROMOLITH SpeedROD 4.6 x 50 mm (4 min.); Solvent A = 10% MeOH, 90% H2O, 0.2% H3PO4; Solvent B = 90% MeOH, 10% H2O, 0.2% H3PO4. LC/MS M+1 = 167.3

The synthetic route of 874-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric, J.; PITTS, William, J.; WATTERSON, Scott, Hunter; WO2010/85584; (2010); A1;,
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