Pyridine → 3-(1-(Benzyloxyimino)ethyl)benzonitrile

HRID 2296967Notes

Reaction equation

HRID 2296967 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8])(=O)[CH3:2].Cl.[CH2:13]([O:20][NH2:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1>CO>[CH2:13]([O:20][N:21]=[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8])[CH3:2])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 802223-AcetylbenzonitrileHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 734333243-(1-(Benzyloxyimino)ethyl)benzonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 14.52 g (0.10 mol) of 3-acetylbenzonitrile in 100 ml of methanol was added 17.56 g (0.11 mol) of O-benzylhydroxyamine hydrochloride and further added dropwise 9.49 g (0.12 mol) of pyridine. The mixture was stirred at room temperature for 2.5 hours, and most of the methanol was distilled off. To the residue was added ethyl acetate and resultant mixture was washed successively with about 5% aqueous hydrochloric acid twice, an about 5% aqueous solution of sodium bicarbonate once, and water once, then dried and concentrated to obtain 24.15 g (95.0 mmol) of crude 3-(1-(benzyloxyimino)ethyl)benzonitrile.

Workup

  1. distillationmost of the methanol was distilled off
  2. additionTo the residue was added ethyl acetate and resultant mixture
  3. washwas washed successively with about 5% aqueous hydrochloric acid twice
  4. dry with materialan about 5% aqueous solution of sodium bicarbonate once, and water once, then dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b0f89e48a1734815b6a2a601a6083b09
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

Loading…