2-Nitrobenzaldehyde → N-[(2-Nitrophenyl)methylidene]hydroxylamine

HRID 580096Notes

Reaction equation

HRID 580096 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].Cl.[NH2:13][OH:14]>CO.O>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[N:13][OH:14])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 111012-NitrobenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 96097N-[(2-Nitrophenyl)methylidene]hydroxylamineYield 91.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
30 °C

Procedure

52.9 g (0.35 mol) of o-nitrobenzaldehyde was dissolved in 150 ml of methanol and an aqueous solution of 27.8 g (0.38 mol) of hydroxylamine hydrochloride in 35 ml of water was added dropwise over 30 minutes while maintaining the temperature at 30° C. The mixture was stirred at the same temperature for 2 hours and diluted with 300 ml of water. White crystals deposited were filtered, washed with water and dried. Thus, 53 g of o-nitrobenzaldoxime was obtained. Yield 91%; M.P. 95°-98° C.

Workup

  1. filtrationWhite crystals deposited were filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-0fd873e9332f4b63b159dd10584551df
Source dataset
uspto-grants-1988_06
Patent number
US04751328

Reaction notes

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