Hydrochloric Acid → N-[(4-Methoxyphenyl)methylidene]hydroxylamine

HRID 1916772Notes

Reaction equation

HRID 1916772 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.Cl.[NH2:12][OH:13].[OH-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[N:12][OH:13])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312444-MethoxybenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 94712N-[(4-Methoxyphenyl)methylidene]hydroxylamineYield 88.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-methoxybenzaldehyde (5.0 g, 36.8 mmol) in methanol (300 mL) was added hydroxylamine hydrochloride (7.6 g, 110.4 mmol) and 2N NaOH (37 mL, 73.6 mmol). The mixture was stirred at room temperature for 6 hours. The mixture was neutralized to pH 4 by using 1N HCl. Excess methanol was removed in vacuo to precipitate out the oxime. The precipitations were filtered and washed with water. The product was dried under vacuum and yield a white solid (4.9 g, 88%): 1H NMR (270 MHz, acetone-d6) δ 8.07 (s, 1H), 7.55 (d, J=8.2 Hz, 2H), 6.95 (d, J=8.2 Hz, 2H), 3.82 (s, 3H).

Workup

  1. customExcess methanol was removed in vacuo
  2. customto precipitate out the oxime
  3. customThe precipitations
  4. filtrationwere filtered
  5. washwashed with water
  6. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-c6fda48e986b4795aafa7257991c6b85
Source dataset
uspto-grants-2013_12
Patent number
US08618147B2

Reaction notes

Loading…