Hydroxyamine hydrochloride → 4-chloro-1-(2-chlorophenyl)-3-((hydroxyimino)methyl)pyridin-2(1H)-one

HRID 1526345Notes

Reaction equation

HRID 1526345 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[C:4](=[O:15])[C:3]=1[CH:16]=O.Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[C:4](=[O:15])[C:3]=1[CH:16]=[N:19][OH:20]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 1020317144-Chloro-1-(2-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbaldehyde

Product 1

HCID 1177703724-chloro-1-(2-chlorophenyl)-3-((hydroxyimino)methyl)pyridin-2(1H)-oneYield 92.1%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-chloro-1-(2-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbaldehyde obtained in Step B (995 mg), hydroxylamine hydrochloride (516 mg) and sodium acetate (609 mg) in methanol/water (4:1, 12.4 mL) was heated at 75° C. for 2 hr, cooled to room temperature, and poured into ice water. The resulting solid was collected by filtration, washed with water, and dried under reduced pressure to give the title compound (968 mg).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-79c1e74e8fd846e48935e5850d0bf394
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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