4-Nitrobenzaldehyde → p-Nitrobenzaldoxime

HRID 580083Notes

Reaction equation

HRID 580083 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[NH2:13][OH:14].Cl>CO.O>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[N:13][OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 22471726Hydroxylamine dihydr-ochloride

Product 1

HCID 96339p-NitrobenzaldoximeYield 96.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
30 °C

Procedure

453 g (3 mols) of p-nitrobenzaldehyde was dissolved in 1350 ml of methanol and then, an aqueous solution of 241 g (3.3 mols) of hydrochloric acid hydroxylamine hydrochloride in 300 ml of water was added dropwise over 30 minutes while maintaining the reaction temperature at 30° C. Thereafter, stirring was effected at the same temperature for two hours and the mixture was diluted with 2000 ml of water. White crystals deposited were filtered, washed with water and dried. 480 g of p-nitrobenzaldoxime was obtained (yield, 96.5%). M.P. 128° to 131° C.

Workup

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

Sources & evidence

ORD record
ord-43e5868c1ad648ac86e21e30d1b2af03
Source dataset
uspto-grants-1988_06
Patent number
US04751328

Reaction notes

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