Hydroxyamine hydrochloride → HCID 6400952, compound

HRID 1192820Notes

Reaction equation

HRID 1192820 reaction equation
Cl.[NH2:2][OH:3].[CH3:4][NH:5][C:6](=[O:15])[C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>N1C=CC=CC=1>[OH:3][N:2]=[C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:6]([NH:5][CH3:4])=[O:15]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 10877451N-methyl-2-oxo-2-phenylacetamide

Product 1

HCID 6400952HCID 6400952, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydroxylamine hydrochloride (5.96 g, 2.5 eq.) was added to a solution of N-methyl-2-oxo-2-phenylacetamide (5.6 g, 34.3 mmol) in pyridine (25 ml). After stirring for 10 h at room temperature, the excess pyridine was removed in vacuo and the residue was taken up in 250 ml of dichloromethane. The organic phase was washed with 200 ml of water and then again with aqueous hydrochloric acid (0.1 M, 250 ml). The precipitated solid was filtered off, giving 2-(hydroxyimino)-N-methyl-2-phenylacetamide as a yellow solid (2.31 g, pure Z isomer). The filtrate was concentrated by evaporation in vacuo. This gave 4.50 g of 2-(hydroxyimino)-N-methyl-2-phenylacetamide (Z/E=mixture of isomers) as a yellow solid.

Workup

  1. customthe excess pyridine was removed in vacuo
  2. washThe organic phase was washed with 200 ml of water
  3. filtrationThe precipitated solid was filtered off

Sources & evidence

ORD record
ord-3a6b693839be4a0aaf45d529f4caa07e
Source dataset
uspto-grants-2014_03
Patent number
US08680283B2

Reaction notes

Loading…