Some common heterocyclic compound, 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, molecular formula is C7H5N3O2, 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: 6393-40-4
3-Nitro-4-aminobenzonitrile (3.00 g) was dissolved in ethanol (300 ml) and added with stannous chloride dihydrate (20.7 g) and the whole was heated to 60C. Sodium borohydride (348 mg) was gradually added thereto and the whole was stirred overnight at 60C. After completion of the reaction, the resultant was added with water (300 ml) and neutralized with a 5 mol/l sodium hydroxide aqueous solution. After ethanol was distilled off under reduced pressure, the aqueous layer was added with ethyl acetate for extraction. The organic layer was washed with a saturated saline solution and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was recrystallized, thereby obtaining the subject compound (1.11 g) as a brown crystal. MS(EI):m/z=133[M]+ 1H-NMR(500MHz,CDCl3):delta=6.68(1H,d,J=8,1Hz),6.95(1H,s),7.05(1H,d,J=8.1Hz).3-Nitro-4-amino-benzonitrile (4.38 g) was dissolved in ethanol (600 ml) and added with stannous chloride dihydrate (34.6 g) and the whole was heated to 60C. Sodium borohydride (366 mg) was gradually added thereto and the whole was stirred overnight at 60C. After completion of the reaction, the resultant was filtrated through Celite and the filtrate was subjected to distillation of the solvent under reduced pressure. The residue was dissolved in chloroform, washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was allowed to recrystallize (hexane/ethyl acetate), thereby obtaining the subject compound (2.56 g) as a brown crystal. MS (EI) :m/z=133[M]+ 1H-NMR(500MHz,CDCl3):delta=6.68(1H,d,J=8.1Hz),6.95(1H,s),7.05(1H, d,J=8.1Hz).An ethanol solution (300 ml) containing 4-amino-3-nitrobenzonitrile (3.00 g) was added with stannous chloride dihydrate (20.7 g) and then added with sodium borohydride (348 mg) . The whole was stirred overnight at 60C. After that, the resultant was subjected to distillation until the amount of the solution became about 100 ml. The resultant was added with water (100 ml) and a large amount of solid component was generated. The resultant was added with a 5 mol/l sodium hydroxide aqueous solution (42 ml) to adjust to pH 7. The solvent was distilled off. The solid component was filtrated out through Celite and washed with methanol and ethyl acetate in the stated order. The filtrate was again filtrated through Celite and only organic solvent was distilled off under reduced pressure. The remaining aqueous layer was subjected to extraction with ethyl acetate and dried with anhydrous magnesium sulfate , and the solvent was distilled off, thereby obtaining the subject compound (2.29 g) as a khaki crystal.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6393-40-4, its application will become more common.
Reference:
Patent; Kureha Corporation; EP1724263; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts