4-Chlorophenyl cyclopropyl ketone → (4-chlorophenyl)(cyclopropyl)methanone O-methyl oxime

HRID 423023Notes

Reaction equation

HRID 423023 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH:14]2[CH2:16][CH2:15]2)=O)=[CH:8][CH:7]=1>N1C=CC=CC=1>[CH3:3][O:2][N:4]=[C:12]([C:9]1[CH:8]=[CH:7][C:6]([Cl:5])=[CH:11][CH:10]=1)[CH:14]1[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 811484-Chlorophenyl cyclopropyl ketoneHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 73696106(4-chlorophenyl)(cyclopropyl)methanone O-methyl oximeYield 87.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

Methoxylamine hydrochloride (2.004 g) was added to (4-chlorophenyl)(cyclopropyl)methanone (2.71 g) in pyridine (60 mL) at 25° C. The resulting solution was stirred at 25° C. for 24 hours. The pyridine was removed in vacuo, and the residual solid extracted with ether. Filtration and evaporation of the solvent gave the crude (4-chlorophenyl)(cyclopropyl)methanone O-methyl oxime (2.75 g, 87%) as a yellow oil. This material was used directly in the next step without further purification.

Workup

  1. customThe pyridine was removed in vacuo
  2. extractionthe residual solid extracted with ether
  3. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-820c7f43ceda4a6a8685cd0aafeb45e2
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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