Dimethylformamide → 4-Amino-3-(hydroxymethyl)benzonitrile

HRID 2286860Notes

Reaction equation

HRID 2286860 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7](I)=[CH:6][C:3]=1[CH2:4][OH:5].[CH3:11][N:12](C)C=O>O>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([C:11]#[N:12])=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 142210292-Amino-5-iodobenzenemethanol

Product 1

HCID 234604924-Amino-3-(hydroxymethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-5-iodobenzyl alcohol (12 g.) and cuprous cuyanide (5.4 g.) in dry dimethylformamide (10 ml.) were heated on a steam-bath for 30 hours, then cooled to ambient temperature and poured into a solution of ferric chloride (10 g.) in water (100 ml.). This mixture was exhaustively extracted with ether (14×60 ml.), the extracts were combined and dried, and the solvent was evaporated. The residue was chromatographed on a column of "Merck 7734" silica, and elution with ether yielded the required 4-amino-3-hydroxymethylbenzonitrile as a buff-coloured solid.

Workup

  1. extractionThis mixture was exhaustively extracted with ether (14×60 ml.)
  2. customdried
  3. customthe solvent was evaporated
  4. customThe residue was chromatographed on a column of "Merck 7734" silica, and elution with ether

Sources & evidence

ORD record
ord-210611d1104e4345903b9eecba29d500
Source dataset
uspto-grants-1981_05
Patent number
US04268510

Reaction notes

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