The reduction of Schiff bases by Grignard reagents with the addition of cobaltous chloride

Abstract

PhCH:NBu (I) (0.05 mole) and 0.10 mole iso-PrMgBr in ethereal soln. kept 4 hrs. at 55 Deg and the product hydrolyzed gave 31.8% PhCH(NHBu)CHMe2 (II) and PhCH2NHBu (III). In the presence of 0.0025 mole MnCl2 (CA 53, 21735d; 55, 18634c), the chief product was [Ph(BuNH)CH]2. With all the other investigated metal salts, only III was produced. In the presence of 0.0025 mole CoCl2, III was produced in 98% yield in 10 minutes; no traces of I, II, or IV could be detected among the products.