3-Aminobenzonitrile

BROWN CRYSTALLINE SOLID

3-Aminobenzonitrile was used in the synthesis of series of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)pyrazoles. It was also used in the preparation of highly substituted γ-lactam analogues of a thiazolidinone follicle stimulating hormone receptor agonist.

3-Aminobenzonitrile on condensation reaction with 4-isothiocyanato-4-methyl pentane-2-one gives condensed monocyclic pyrimidine derivatives.

Dehydration: In the 1000ml reaction flask with brine-cooled reflux device, add 510g of toluene, 102g of 3-aminobenzamide (0.75mol), raise the temperature to 90-100, slowly add 205g of sulfoxide chloride (1.72mol), there is a large amount of off-gas generation (HCl + SO2), sulfoxide drops after the end of, and continue to hold the temperature to the material is all dissolved clear and no off-gas After the sulfoxide chloride drop, continue to keep warm until the material is all dissolved and no exhaust gas is released. Cooled to 50 ~ 60 , that is, the dehydration of liquid, insulation for use. _x000D
Hydrolysis: add 102g of water in 1000ml reaction bottle, stirring temperature to 50-60 , add the above dehydration solution, at this time there is tail gas (SO2), control the drop acceleration, drop stirring to no tail gas release, while hot, 30% sodium hydroxide solution to adjust the aqueous layer of pH to 6.5-7.5. Static layering, the organic layer of slow stirring and cooling to 0-5 , filtration, appropriate amount of 0-5 toluene wash, filtering, and the water is not used. Appropriate amount of 0-5 toluene washing, drying to obtain m-aminobenzonitrile 80.8g, yield 91.3%, GC purity 99.6%.