Pyridine → HCID 86669068, compound

HRID 1807400Notes

Reaction equation

HRID 1807400 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]1[CH2:10][C@H:9]1[C:11](=O)[CH3:12].N1C=CC=CC=1.Cl.[CH3:21][O:22][NH2:23]>CO.O>[CH3:21][O:22][N:23]=[C:11]([C@@H:9]1[CH2:10][C@H:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:12]

Participants

6

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 29079050HCID 29079050, compound

Product 1

HCID 86669068HCID 86669068, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of trans 1-[2-(2-chloro-phenyl)-cyclopropyl]-ethanone (1.0 g; 5.1 mmol) in methanol (10 ml) at ambient temperature was added pyridine (0.85 ml; 10 mmol) and methoxyamine hydrochloride (0.86 g; 10 mmol). The reaction mixture was stirred for 16 hours at ambient temperature then poured in water (50 mL) and extracted with dichloromethane (3×30 ml). Combined organic layers were dried over anhydrous sodium sulphate. The solvent was removed in vacuo to afford 1.1 g (98% of theory) of trans 1-[2-(2-chloro-phenyl)-cyclopropyl]-ethanone O-methyl-oxime as an oil.

Workup

  1. extractionextracted with dichloromethane (3×30 ml)
  2. dry with materialCombined organic layers were dried over anhydrous sodium sulphate
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f7f8c22896454442b27d004c37f98612
Source dataset
uspto-grants-2013_01
Patent number
US08357635B2

Reaction notes

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