Hydroxyamine hydrochloride → 4-Bromo-3-methylbenzaldehyde oxime

HRID 1741070Notes

Reaction equation

HRID 1741070 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[CH3:10].Cl.[NH2:12][OH:13]>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:12][OH:13])=[CH:4][C:3]=1[CH3:10]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 109215214-Bromo-3-methylbenzaldehyde

Product 1

HCID 738479544-Bromo-3-methylbenzaldehyde oximeYield 64.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-bromo-3-methylbenzaldehyde (D80) (1 g; 0.005 mol) in methanol (20 ml) was treated with hydroxylamine hydrochloride (700 mg, 0.01 mol) and the mixture stood at room temperature over a weekend. The solvent was evaporated under reduced pressure and the residual solid was partitioned between saturated K2CO3 solution and ethyl acetate. The organic phase was dried (Na2SO4), concentrated in vacuo and the residue purified by chromatography on silica gel eluting with 60-80 petroleum-ether and ethyl acetate, to afford the title compound as a pale pink powder (693 mg, 20%).

Workup

  1. waitthe mixture stood at room temperature over a weekend
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residual solid was partitioned between saturated K2CO3 solution and ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customthe residue purified by chromatography on silica gel eluting with 60-80 petroleum-ether and ethyl acetate

Sources & evidence

ORD record
ord-1d4d92cf97f943a79396f03378c35b92
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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