Hydroxyamine hydrochloride → 3-Methoxy-4-nitrobenzaldehyde oxime

HRID 509450Notes

Reaction equation

HRID 509450 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH:6]=O.Cl.[NH2:15][OH:16]>CCO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH:6]=[N:15][OH:16]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 114920433-Methoxy-4-nitrobenzaldehyde

Product 1

HCID 1317332503-Methoxy-4-nitrobenzaldehyde oximeYield 75.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To 3-methoxy-4-nitrobenzaldehyde (53.5 g, 295.5 mmol)) in EtOH (285 ml) was slowly added a solution of hydroxylamine hydrochloride (30.8 g, 443 mmol) in water (50 ml). The reaction mixture was stirred overnight, poured into ice-cold water, and the formed precipitate was collected by filtration to furnish 44 g of 3-methoxy-4-nitrobenzaldehyde oxime. The filtrate was extracted with DCM, and the organic phase was washed with water and brine, dried over sodium sulfate, and concentrated to furnish additional 8.2 g of the title product. 1H NMR (CDCl3) δ: 8.13 (s, 1H), 7.87 (d, J=8.2 Hz, 1H), 7.51 (s, 1H), 7.35 (s, 1H), 7.18 (dd, J=8.4, 1.4 Hz, 1H), 4.01 (s, 3H).

Workup

  1. additionpoured into ice-cold water
  2. filtrationthe formed precipitate was collected by filtration

Sources & evidence

ORD record
ord-6f8d254976794bed9fa60fcabf2c3b2f
Source dataset
uspto-grants-2015_08
Patent number
US09096582B2

Reaction notes

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