3-Methoxybenzaldehyde → N-[(3-Methoxyphenyl)methylidene]hydroxylamine

HRID 2111670Notes

Reaction equation

HRID 2111670 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O>O>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[N:2][OH:3]

Participants

5

Reactant 3

HCID 115693-MethoxybenzaldehydeHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 293577N-[(3-Methoxyphenyl)methylidene]hydroxylamineYield 103.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of hydroxylamine hydrochloride (10 g, 0.144 mol) in distilled water (20 ml) was added to 20%(w/v) aqueous sodium hydroxide solution (28 ml). 3-Methoxybenzaldehyde (14 ml, 0.12 mol) was added in one portion and the mixture was stirred for 2 hours at 0-5° C. The mixture was adjusted to pH7 and extracted with dichloromethane. The extracts were combined, dried (MgSO4) and the solvent removed by evaporation to give the title compound (18.7 g, 100%) as a colourless oil. NMR (CDCl3): 3.8 (s, 3H), 6.9 (m, 1H), 7.1 (m, 2H), 7.15 (m, 1H), 8.1 (s, 1H), 8.6 (br s, 1H).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-75b8645a954943b08d7770bcfbaa5034
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Reaction notes

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