Sodium cyanoborohydride → 5-(2-[-4-(4,N-Dimethylanilino)-2-Butylamino]-1-Hydroxyethyl)Salicylamide

Participants

Reaction Steps

To a solution of 20 mmol 5-(2-amino-1-hydroxyethyl)salicylamide and 5.7 g (30 mmol) 4-(N,4-dimethylanilino)-2-butanone [b.p. 93°-6°/0.1 mm, prepared by procedure of Craig, et al, J. Org. Chem., 29, 410 (1964)] in 150 ml methanol, add 1.9 g (30 mmol) NaCNBH3. After 20 hrs., concentrate, and partition between EtOAc and 1.0 N NaHCO3 solution. Dry and concentrate. Warm the foam with EtOAc to give a white solid, m.p. 123°-6°.

Provenance & Evidence