Application of 621-50-1,Some common heterocyclic compound, 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, molecular formula is C8H6N2O2, 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.
N-[3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-phenyl]-methanesulfonamide hydrochloride 1-Chloromethyl-3-nitro-benzene (5 g) and 4.28 g of sodium cyanide were dissolved in a mixture of 15 ml of water and 50 ml of dioxane and the two phase mixture was heated to 100C for 12 hr. The dioxane was removed by evaporation and the aqueous solution was extracted with dichloromethane. The organic extract was washed with brine, dried, and evaporated. The residue was purified by flash column chromatography eluding with EtOAc:hexane (1:4) to afford 2.86 g of a tan solid, mp 51.7-52.7C, of (3-nitro-phenyl)-acetonitrile. (3-Nitro-phenyl)-acetonitrile (2.79g) was dissolved in 50 ml of ethyl acetate and the mixture was treated with 19.5 g of tin (II) chloride dihydrate and stirred at room temperature for 72 hr. The mixture was diluted with ethyl acetate and treated with saturated sodium bicarbonate solution, separated, and extracted with ethyl acetate. The extracts were combined, dried, and evaporated, leaving 2.1 g of tan oil of (3-amino-phenyl)-acetonitrile.
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-Nitrophenyl)acetonitrile, its application will become more common.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; EP887346; (1998); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts