Hydroxyamine hydrochloride → 4-(5-Isoxazolyl)benzonitrile

HRID 1370073

Reaction equation

HRID 1370073 reaction equation
Cl.NO.[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:18])[CH:13]=[CH:14][N:15](C)C)=[CH:8][CH:7]=1)#[N:5]>CO.O>[O:18]1[C:12]([C:9]2[CH:10]=[CH:11][C:6]([C:4]#[N:5])=[CH:7][CH:8]=2)=[CH:13][CH:14]=[N:15]1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 28059521-(4-Cyanophenyl)3-dimethylaminopropen-1-one

Product 1

HCID 185170264-(5-Isoxazolyl)benzonitrileYield 89.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Hydroxylamine hydrochloride (21.40 g, 308 mmol) was added to a suspension of 1-(4-cyanophenyl)-3-dimethylaminopropen-1-one (55.96 g, 280 mmol) in MeOH (450 ml) and the reaction stirred at room temperature for 24 h. The reaction was diluted with water (400 ml) and the resultant precipitate collected by filtration, washed with water (5×150 ml) and dried in vacuo to give 4-(5-isoxazolyl)-benzonitrile as a pale yellow solid (42.53 g) m.p. 148-149°. δH (CDCl3) 8.35 (1H, d, J 1.8 Hz), 7.91 (2H, d, J 8.3 Hz), 7.77, (2H, d, J 8.3 Hz), 6.66 (1H, d, J 1.8 Hz).

Workup

  1. filtrationthe resultant precipitate collected by filtration
  2. washwashed with water (5×150 ml)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e0bfba8e587149d98e74c6fc92d98298
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Linked notes

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