Pyridine → Methyl methoxyimino-[2-(1-(4-chlorophenyl)-3-pyrazolyloxy)pyridin-3-yl]acetate

HRID 279045Notes

Reaction equation

HRID 279045 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([O:13][C:14]3[C:19]([C:20](=O)[C:21]([O:23][CH3:24])=[O:22])=[CH:18][CH:17]=[CH:16][N:15]=3)=[N:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl.[CH3:33][O:34][NH2:35]>CO>[CH3:33][O:34][N:35]=[C:20]([C:19]1[C:14]([O:13][C:10]2[CH:11]=[CH:12][N:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=2)=[N:15][CH:16]=[CH:17][CH:18]=1)[C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 17888488Methyl [2-(1-(4-chlorophenyl)-3-pyrazolyloxy)pyridin-3-yl]glyoxylate

Product 1

HCID 85060149Methyl methoxyimino-[2-(1-(4-chlorophenyl)-3-pyrazolyloxy)pyridin-3-yl]acetateYield 42.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.7 g (7.3 mmol) of methyl [2-(1-(4-chlorophenyl)-3-pyrazolyloxy)pyridin-3-yl]glyoxylate (Example 1a.), 1.16 g of pyridine and 25 ml of methanol were admixed with 0.67 g (8.0 mmol) of O-methylhydroxylamine hydrochloride, and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was separated off and washed with ice-cold methanol. The residue was freed from the solvent under reduced pressure. 1.2 g (42%) of the title compound were obtained as a white solid.

Workup

  1. customThe resulting precipitate was separated off
  2. washwashed with ice-cold methanol

Sources & evidence

ORD record
ord-6da669d37e6a45a48445a53b98f6e262
Source dataset
uspto-grants-2002_03
Patent number
US06362192B1

Reaction notes

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