O-Methylhydroxylamine hydrochloride → 1-(2-Hydroxyphenyl)-2-nitroethanone O-methyloxime

HRID 2304887Notes

Reaction equation

HRID 2304887 reaction equation
Cl.[CH3:2][O:3][NH2:4].[OH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=O)[CH2:13][N+:14]([O-:16])=[O:15]>CO>[CH3:2][O:3][N:4]=[C:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[OH:5])[CH2:13][N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 12258642o-Hydroxy-omega-nitroacetophenone

Product 1

HCID 1361444021-(2-Hydroxyphenyl)-2-nitroethanone O-methyloximeYield 77.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
47.5 °C

Procedure

At 20° C., 73.5 g (0.88 mol) of methoxyamine hydrochloride are added to a solution of 80.0 g (0.44 mol) of o-hydroxy-ω-nitroacetophenone in 500 ml of methanol, and the mixture is stirred at 45 to 50° C. for 8 to 12 hours. The solution is cooled to 20° C., poured into 1 l of ice-water and stirred for one hour. The crystalline product is filtered off and washed with 500 ml of water a little at a time and dried at 40° C. in a vacuum drying cabinet. 72 g (74.6% of theory) of 1-(2-hydroxyphenyl)-2-nitro-ethanone O-methyl-oxime are obtained as a mixture of stereoisomers.

Workup

  1. temperatureThe solution is cooled to 20° C.
  2. stirringstirred for one hour
  3. filtrationThe crystalline product is filtered off
  4. washwashed with 500 ml of water a little at a time
  5. customdried at 40° C. in a vacuum
  6. customdrying cabinet

Sources & evidence

ORD record
ord-6d9dba821f0f45be93df16843134b5bf
Source dataset
uspto-grants-2002_08
Patent number
US06437153B1

Reaction notes

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