Author: Jessica.F

Electric Literature of 77326-36-4,Some common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, molecular formula is C7H5FN2, 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.

Sodium hydride (0.154 g, 3.85 mmol, 1.5 equiv) was added to a mixture of 2-amino-6-fluorobenzonitrile (0.524 g, 3.85 mmol, 1.5 equiv) and 2-methyl-2-((5-methylpyrimidin-2-yl)amino)propan-1-ol (Example 1b, 0.465 g,2.56 mmol, 1 equiv) in anhydrous THF (25 mL) under nitrogen. The reaction mixture was stirred for 10 minutes at room temperature and refluxed for 21 h. The reaction mixture was concentrated and the residue was purified by chromatography on a silica(50% EtOAc in Hexanes gradient) to provide the title compound (611 mg, 80% yield), MS 298 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-6-fluorobenzonitrile, its application will become more common.

Reference:
Patent; FIRMENICH INCORPORATED; FOTSING, Joseph, R.; TACHDJIAN, Catherine; SERVANT, Guy; CHING, Brett, Weylan; DAVIS, Timothy; (94 pag.)WO2020/33420; (2020); A1;,
Nitrile – Wikipedia,
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Reference of 2973-50-4, These common heterocyclic compound, 2973-50-4, name is 2-(2-Aminophenyl)acetonitrile, 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.

General procedure: In an Erlenmeyer flask, 2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetohydrazide (4) (1.0 mmol), aromatic nitriles (1.0 mmol) and DMAP (30 mol%) were taken in ethanol (15 mL). The reaction mixture was irradiated inside a synthetic microwave oven (Make-Ethosi Milestone with temperature control) for about 20-25 min (700 W). After completion of reaction (monitored by TLC), the mixture was concentrated to obtain the solid product. The solid product formed was filtered, dried and recrystallized from ethanol.

Statistics shows that 2-(2-Aminophenyl)acetonitrile is playing an increasingly important role. we look forward to future research findings about 2973-50-4.

Reference:
Article; Sangshetti, Jaiprakash N.; Kalam Khan, Firoz A.; Chouthe, Rashmi S.; Damale, Manoj G.; Shinde, Devanand B.; Chinese Chemical Letters; vol. 25; 7; (2014); p. 1033 – 1038;,
Nitrile – Wikipedia,
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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 654-70-6 as follows. HPLC of Formula: C8H5F3N2

2-Isopropoxy-benzoyl chloride was condensed with 4-Amino-2-trifluromethyl benzonitrile in dichloromethane in presence of triethylamine as acid scavenger to yield N-4-Cyano-3-trifluoromethyl-phenyl)-2-Isopropoxy-benzamide. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product. 1H-NMR:delta6.95-8.01 (7H,aromatic), delta4.04(1H,m,OCH), delta1.38(6H,d,Methyl)

According to the analysis of related databases, 654-70-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kundu, Tapas Kumar; Balasubramanyam, Karanam; Swaminathan, Vankatesh; US2006/167107; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 6621-59-6, name is 6-Bromohexanenitrile, 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 6621-59-6, Safety of 6-Bromohexanenitrile

General procedure: A solution of the corresponding precursor (4-chlorobutyronitrile for compounds 1, 5-chlorovaleronitrile for compounds 3 and 6-bromohexanenitrile for compounds 6) (2.5 mmol) in dimethylformamide (1 mL) was added during 1.5 h to a mixture of the arylamine (2.5 mmol), Cs2CO3(2.5 mmol) and KI (5 mmol) in dimethylformamide (2.5mL). The mixture was stirred at the indicated temperature and time. After completion of the reaction, as indicated by TLC, the mixture was treated with ethyl ether (50 mL) and water (10 mL). The aqueous phase was separated and extracted with ethyl ether (30 mL). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The solvent was evaporated in vacuo. The crude product was purified by column chromatography (silica gel, hexane:DCM).

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

Reference:
Article; Diaz, Jimena E.; Mollo, Maria C.; Orelli, Liliana R.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2026 – 2031;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 53312-81-5, name is 5-Amino-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 53312-81-5, Safety of 5-Amino-2-fluorobenzonitrile

General procedure: To the solution of carboxylic acid (1 eq.) in DCM were added HATU (1.05 eq.), amine (1.1 eq.) and DIPEA (2 eq.). The mixture was stirred for 16 h at room temperature. Afterwards, the solution was washed with water and brine. The resulting organic layer was dried over MgSO4, and the solvent was removed by evaporation. The crude material was purified by flash chromatography (CH2Cl2:MeOH).

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, 5-Amino-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Egyed, Attila; Bajusz, David; Keser?, Gyoergy M.; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1497 – 1508;,
Nitrile – Wikipedia,
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Application of 591769-05-0,Some common heterocyclic compound, 591769-05-0, name is 3-Cyclopentylacrylonitrile, molecular formula is C8H11N, 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 4-(lH-pyrazol-4-yl)pynOlo[l,2-b]pyridazine-3-carbonitrile 16a (60 mg, 0.287 mmol) in DMF (1.5 mL) was added 3-cyclopentylacrylonitrile (109 mg, 0.717 mmol), 2,3,4,6,7,8,9, 10-octahydropyrimido[l,2-a]azepine (0.270 mL, 1.772 mmol) and heated with stirring at 50 °C for 3 h. The reaction mixture was cooled to RT and concentrated in vacuum to dryness. The residue obtained was purified by combiflash column chromatography [silica gel, 4 g eluting with hexanes/ethyl acetate (1 :0 to 2:1)] to give 4-(l-(2-cyano-l-cyclopentylethyl)-lH- pyrazol-4-yl)pyrrolo[l,2-b]pyridazine-3-carbonitrile 16b (56 mg, 59percent, Rf = 0.42 with hexanes/ethyl acetate = 2:1) as a yellow solid; 1H NMR (300 MHz, OMSO-d6) delta 8.80 (d, J= 0.6 Hz, 1H), 8.48 (s, 1H), 8.31 (s, 1H), 8.19 (t, J= 2.1 Hz, 1H), 7.13 (d, J= 2.0 Hz, 2H), 4.64 (td, J = 9.0, 4.8 Hz, 1H), 3.29 – 3.21 (m, 2H), 2.48 – 2.37 (m, 1H), 1.91 – 1.11 (m, 8H).

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

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda, S.; KOTIAN, Pravin, L.; WU, Minwan; WO2011/150356; (2011); A1;,
Nitrile – Wikipedia,
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Electric Literature of 5312-97-0, A common heterocyclic compound, 5312-97-0, name is 2,5-Dimethoxybenzonitrile, molecular formula is C9H9NO2, 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.

General procedure: Dry HCl (g) was bubbled into a stirred solution of nitrile (10 mmol) in propargyl alcohol (1 equiv.) at 0 C for 10 minutes. The vial was capped and stirred warming to rt overnight (18 h). Air was bubbled through the resulting mixture for 10 minutes. The mixture was then diluted with Et2O (20 mL), and the resulting precipitate was collected by vacuum filtration, and washed with Et2O (20 mL). This salt was suspended in CHCl3 (50 mL), to which saturated NaHCO3 (50 mL) was then added. After mixing, the layers were separated, and the aqueous layer was extracted with an additional amount of CHCl3 (20 mL). The combined organic layers were dried over Na2SO4 and concentrated to afford the imidate.

The synthetic route of 5312-97-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fricke, Patrick J.; Stasko, Jenna L.; Robbins, Dylan T.; Gardner, Alexander C.; Stash, Jacqueline; Ferraro, Mark J.; Fennie, Michael W.; Tetrahedron Letters; vol. 58; 48; (2017); p. 4510 – 4513;,
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Synthetic Route of 89001-53-6, A common heterocyclic compound, 89001-53-6, name is 2-Methyl-4-nitrobenzonitrile, molecular formula is C8H6N2O2, 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.

b) Preparation of 5,6-Dihydro-5-oxo-9-nitro-indeno[1,2-c]isoquinoline (53a); To a refluxing mixture of 2-methyl-4-nitro-benzonitrile (32.4 g, 0.2 mol) and NBS (44.470 g, 0.25 mol) in CCl4 (300 ml) was added AIBN (0.325 g) and the resultant reaction mixture was refluxed for 4 hours. The reaction mixture was treated with AIBN (0.325 g, 31 mmol) and refluxed further for 4 hours. The reaction mixture was filtered, and the filtered succinimide was washed with CCl4. The filtrate was concentrated in vacuo to provide a bromo compound (46 g). The bromo compound was dissolved in MeCN (200 ml), and to the reaction mixture was added homophthalic anhydride (30.780 g, 0.19 mol) at room temperature and under inert atmosphere. The reaction mixture was then treated with a solution of triethylamine (84 ml, 0.6 mol) in acetonitrile (100 ml). The reaction mixture was refluxed for 8 hours. The precipitate that formed was removed by filtration and washed with MeCN (100 ml). The washed precipitate was suspended in DMF (300 ml), which was heated at 130 C., then cooled and filtered. The resultant solid was washed with DMF (100 ml) and dried under vacuum to provide Compound 53a as a pale yellow solid (18.310 g, 33%). 1H-NMR (DMSO-d6): delta, 4.09 (s, 2H), 7.56 (m, 1H), 7.81-7.82 (m, 2H), 8.17 (d, J=8.4 Hz, 1H), 8.26-8.34 (m, 2H), 8.44 (s, 1H), 12.47 (s, 1H).

The synthetic route of 89001-53-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Inotek Pharmaceuticals Corporation; US2006/287313; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 103146-25-4, These common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(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.

A test tube equipped with a stopper was charged with 10 mg (0.029 m mol) of [(=T :)-4-] [4-dimethylamino-1- (4′-fluorophenyl)-1-hydroxybutyl]-3-hydroxymethylbenzonitrile, 10 mg of Novozym 435 (product of NOvozymes), 33 mg (0.29 [M MOL)] of vinyl butyrate and 1 ml of various kinds of solvents, and stirred at [30C] for 16 hours. After the reaction, converted ratios and optical purities were analyzed and E-values were calculated. The results are shown in Table 9.

The synthetic route of 103146-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 3598-13-8, name is 2-(4-Chlorophenoxy)acetonitrile, 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 3598-13-8, HPLC of Formula: C8H6ClNO

2-(3-(hydroxymethyl)-6-nitro-2,3-dihydrobenzo[b][l,4]dioxin-5-yl)acetonitrile: A solution of racemic (7-nitro-2,3-dihydrobenzo[b][l,4]dioxin-2-yl)methanol (1.00 g, 4.73 mmol) and 4-chlorophenoxyacetonittauile (827 mg, 4.94 mmol) in DMF (12 mL) was added dropwise to a solution of potassium tert-butoxide (2.12 g, 18.9 mmol) in DMF (20 mL) at -5- 00C. After the addition was complete (7 minutes), the reaction mixture was stirred for 1 hour at -5-00C. The reaction mixture was acidified with 1 N HCl before drowning into water (200 mL). The mixture was extracted with EtOAc (3 x 100 mL) and the combined organic layers were washed with IN NaOH (3 x 50 mL) to remove most of the 4-chlorophenol. After removal of solvent, the residue was purified by flash chromatography on silica gel, gradient elution using 2:3, 1 :1, 3:2, 100:0 ethyl acetate/hexane, to give 139 mg, 14% recovered starting material and 804 mg, 68% yield of the title compound as a solid. 1H NMR (CDCl3) 5 7.77 (IH, d, J=9.12 Hz); 7.01 (IH, d, J=9.12 Hz); 4.50-4.40 (2H, m); 4.30-3.91 (5H, m); 2.25-2.21 (IH, m). 13C NMR (CDCl3) 5 148.07, 141.71, 141.55, 119.44, 117.07, 116.96, 115.71 , 74.36, 65.31, 61.18, 14.89.

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-(4-Chlorophenoxy)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; WO2007/139998; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts