Methanol → HCID 12814740, compound

HRID 972065Notes

Reaction equation

HRID 972065 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]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 4586991-(N-methylanilino)propan-2-oneHCID 5003444Sodium cyanoborohydrideHCID 70613586HCID 70613586, compound

Product 1

HCID 12814740HCID 12814740, compound

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°.

Workup

  1. concentration, concentrate
  2. custompartition between EtOAc and 1.0 N NaHCO3 solution
  3. customDry
  4. concentrationconcentrate the organic layer
  5. dissolutionDissolve the foam in CHCl3
  6. washwash with water
  7. filtrationFilter the solid which forms
  8. customrecrystallize from EtOAc
  9. customto give a white solid, mp 143°-5°

Sources & evidence

ORD record
ord-4c7dec0d11964136a92689c4decdd1cc
Source dataset
uspto-grants-1979_07
Patent number
US04163053

Reaction notes

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