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

HRID 972067Notes

Reaction equation

HRID 972067 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].[Cl:15][C:16]1[CH:28]=[CH:27][C:19]([N:20]([CH2:22][CH2:23][C:24](=O)[CH3:25])[CH3:21])=[CH:18][CH:17]=1.[BH3-]C#N.[Na+]>CO>[Cl:15][C:16]1[CH:28]=[CH:27][C:19]([N:20]([CH2:22][CH2:23][CH:24]([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])[CH3:25])[CH3:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 155656635-(2-Amino-1-hydroxyethyl)-2-hydroxybenzamideHCID 203964554-(4-chloro-N-methylanilino)-2-butanone

Product 1

HCID 540530485-(2-[4-(4-Chloro-N-Methylanilino)-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 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°.

Workup

  1. concentrationconcentrate
  2. custompartition between EtOAc and 1.0 N NaHCO3 solution
  3. washWash the organic layer with 1.0 N HCl
  4. extractionNeutralize the aqueous portion with NaHCO3 and extract with EtOAc
  5. customDry
  6. concentrationconcentrate
  7. customrecrystallize the residue from EtOAc-hexane
  8. customto give a white solid, mp 127°-9°

Sources & evidence

ORD record
ord-ff356d30e83947f4842fc3eec7f783ac
Source dataset
uspto-grants-1979_07
Patent number
US04163053

Reaction notes

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