Methanol → 5-(2-[3-(N-Methylanilino)-2-Propylamino]-1-Hydroxyethyl)Salicylamide
Reaction equation
[NH2:1][CH:2](O)[CH2:3][C:4]1[CH:12]=[C:8]([C:9]([NH2:11])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1.[CH3:15][N:16]([CH2:23][C:24](=O)[CH3:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH3-]C#N.[Na+].C[OH:32]>>[CH3:15][N:16]([CH2:23][CH:24]([NH:1][CH2:2][CH:3]([C:4]1[CH:12]=[C:8]([C:9]([NH2:11])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1)[OH:32])[CH3:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Participants
5
Procedure
To To a solution of 20 mmol 5-(2-amino-hydroxyethyl)salicylamide and 3.26 g (20 mmol) N-methylanilino acetone in 100 ml methanol add 2.51 g (40 mmol) NaCNBH3. Stir 16 hrs., concentrate, and partition between EtOAc and 1.0 N NaHCO3 solution. Dry and concentrate the organic layer. Dissolve the foam in CHCl3, and wash with water. Filter the solid which forms and recrystallize from EtOAc to give a white solid, mp 143°-5°.