Hydroxyamine hydrochloride → 1-(4-Fluorophenyl)-2-pyridin-2-ylethanone Oxime

HRID 2300190Notes

Reaction equation

HRID 2300190 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][CH:3]=1.Cl.[NH2:18][OH:19].C([O-])(=O)C.[Na+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:18][OH:19])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 36168691-(4-Fluorophenyl)-2-pyridin-2-ylethanone

Product 1

HCID 880148471-(4-Fluorophenyl)-2-pyridin-2-ylethanone OximeYield 87.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-2-pyridin-2-ylethanone (6.27 g 29 mmol) in methanol (100 ml) was added a solution of hydroxylamine hydrochloride (9.6 g 130 mmol) and sodium acetate (15.6 g) in water (80 ml) and the reaction was stirred at room temperature for 24 hours. The resulting precipitate was filtered off and dried to give the title compound as a white solid (5.83 g 87%). (M-H2O)H+: 213; NMR: (CDCl3): δ 4.42 (2H, s) 7.00 (2H, t) 7.14 (1H, m) 7.28 (1H, d) 7.59 (1H, dt) 7.72 (2H, m) 8.55 (1H, m) 8.96 (1H, br).

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. customdried

Sources & evidence

ORD record
ord-3eb63e4daa7647e39e34d9153ae39000
Source dataset
uspto-grants-2002_12
Patent number
US06498166B1

Reaction notes

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