4-Methoxybenzaldehyde → N-[(4-Methoxyphenyl)methylidene]hydroxylamine

HRID 2186206Notes

Reaction equation

HRID 2186206 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.Cl.[OH:12][NH2:13].C([O-])(=O)C.[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[N:13][OH:12])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 94712N-[(4-Methoxyphenyl)methylidene]hydroxylamineYield 115.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

4-Methoxybenzaldehyde (10.0 g, 73.4 mmol) was dissolved in 200 mL of ethanol. A solution of hydroxyamine hydrochloride (6.38 g, 91.8 mmol) in 50 mL of H2O was added followed by a solution of sodium acetate (12.1 g, 146.8 mmol) in 50 mL of H2O. The mixture was stirred at room temperature under N2 for 12 h. The ethanol was removed in vacuo and the aqueous mixture was extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, and concentrated to afford 12.8 g of light yellow oil. 1H NMR showed it was 80% pure (92% yield). This material was taken into the next step without further purification. (CDCl3): δ2.15 (s, 1H); 3.83 (s, 3H); 6.92 (d, 2H); 7.50 (d, 2H); 8.10 (s, 1H).

Workup

  1. customThe ethanol was removed in vacuo
  2. extractionthe aqueous mixture was extracted with EtOAc
  3. washThe EtOAc solution was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0b6b4d844ddf406f92ccac9e8d043472
Source dataset
uspto-grants-2002_06
Patent number
US06403620B1

Reaction notes

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