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

HRID 972068Notes

Reaction equation

HRID 972068 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]([CH2:24][CH2:25][C:26](=O)[CH3:27])[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1.[BH3-]C#N.[Na+]>CO>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([N:16]([CH2:24][CH2:25][CH:26]([NH:1][CH2:2][CH:3]([C:5]2[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([OH:14])=[CH:7][CH:6]=2)[OH:4])[CH3:27])[CH3:15])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 155656635-(2-Amino-1-hydroxyethyl)-2-hydroxybenzamideHCID 203964634-(N,4-dimethylanilino)-2-butanone

Product 1

HCID 544964915-(2-[-4-(4,N-Dimethylanilino)-2-Butylamino]-1-Hydroxyethyl)Salicylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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°.

Workup

  1. concentration, concentrate
  2. custompartition between EtOAc and 1.0 N NaHCO3 solution
  3. customDry
  4. concentrationconcentrate
  5. temperatureWarm the foam with EtOAc
  6. customto give a white solid, m.p. 123°-6°

Sources & evidence

ORD record
ord-6918445d86da4a33a30db0c84bd5ca1d
Source dataset
uspto-grants-1979_07
Patent number
US04163053

Reaction notes

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