Hydroxyamine hydrochloride → 5-Hydroxyiminomethyl-2-methylnitrobenzene

HRID 386735Notes

Reaction equation

HRID 386735 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+]>O1CCCC1.O>[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:14][OH:15])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 17989983-Nitro-p-tolualdehyde

Product 1

HCID 536283185-Hydroxyiminomethyl-2-methylnitrobenzeneYield 91.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-methyl-3-nitrobenzaldehyde (3.5 g) in tetrahydrofuran (50 mL) was added dropwise to a solution of hydroxylamine hydrochloride (3.0 g) and sodium acetate (4.0 g) in tetrahydrofuran (50 mL) and water (50 mL) under ice cooling, and, on completion of the dropwise addition, the mixture was stirred for one hour at room temperature. The reaction solution was diluted with water and then extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude product of 4-methyl-3-nitrobenzaldehyde oxime (3.5 g).

Workup

  1. additionon completion of the dropwise addition
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fcf115bd39044ce0ba1f52f96e809d2e
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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