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

Participants

Reaction Steps

To a solution of 20 mmol 5-(2-amino-1-hydroxyethyl)salicylamide and 4.22 g (20 mmol) 4-(4-chloro-N-methylanilino)-2-butanone [mp 60°-1°, prepared by procedure of Craig, et al, J. Org. Chem., 29, 410 (1964)] in 100 ml methanol add 2.52 g (40 mmol) NaCNBH3. Stir 6 days, concentrate, and partition between EtOAc and 1.0 N NaHCO3 solution. Wash the organic layer with 1.0 N HCl. Neutralize the aqueous portion with NaHCO3 and extract with EtOAc. Dry, concentrate, and recrystallize the residue from EtOAc-hexane to give a white solid, mp 127°-9°.

Provenance & Evidence