Stannous chloride dihydrate → 4-[2-(5-Amino-2-methyl-phenylamino)-oxazol-5-yl]-benzonitrile

Participants

Reaction Steps

To a solution of 4-[2-(2-Methyl-5-nitro-phenylamino)-oxazol-5-yl]-benzonitrile (500 mg, 1.56 mmol) in ethanol (15 mL) was added tin(II) chloride dihydrate (677 mg, 3 mmol). The reaction mixture was heated under reflux for 4 h. The mixture was then concentrated, saturated aqueous NaHCO3 was added and the resultant suspension was extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous MgSO4 and concentrated. The residue was alumina column chromatographed (dichloromethane/ethanol: 99/1). 4-[2-(5-Amino-2-methyl-phenylamino)-oxazol-5-yl]-benzonitrile was obtained as pale yellow powder (172 mg, 38%).

Provenance & Evidence