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

HRID 972064Notes

Reaction equation

HRID 972064 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([OH:14])=[CH:7][CH:6]=1)[OH:4].[CH3:15][N:16]([CH2:23][CH2:24][C:25](=O)[CH3:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH3-]C#N.[Na+]>C(O)C>[CH3:15][N:16]([CH2:23][CH2:24][CH:25]([NH:1][CH2:2][CH:3]([C:5]1[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([OH:14])=[CH:7][CH:6]=1)[OH:4])[CH3:26])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 114126874-(Methyl-phenyl-amino)-butan-2-oneHCID 155656635-(2-Amino-1-hydroxyethyl)-2-hydroxybenzamide

Product 1

HCID 537681395-(2-[4-(N-Methylanilino)-2-Butylamino]-1-Hydroxyethyl)Salicylamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 20 mmol 5-(2-amino-1-hydroxyethyl)salicylamide and 3.54 g (20 mmol) 4-(N-methylanilino)-2-butanone [procedure of Craig, et al, J. Org. Chem., 29, 410 (1964)] in 100 ml ethanol add 1.26 g (20 mmol) NaCNBH3. Stir 16 hrs., concentrate, and partition between EtOAc and 1.0 N NaHCO3 solution. Dry and concentrate the organic layer. Recrystallize the residue from methanol to give a white solid, mp 150°-2°.

Workup

  1. concentration, concentrate
  2. custompartition between EtOAc and 1.0 N NaHCO3 solution
  3. customDry
  4. concentrationconcentrate the organic layer
  5. customRecrystallize the residue from methanol
  6. customto give a white solid, mp 150°-2°

Sources & evidence

ORD record
ord-2eb4966462124e42850ae763aa5386e5
Source dataset
uspto-grants-1979_07
Patent number
US04163053

Reaction notes

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