O-Methylhydroxylamine hydrochloride → 2-bromo-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone-O-methyloxime

HRID 56063Notes

Reaction equation

HRID 56063 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[C:10]([Cl:11])=[CH:9][C:8]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[CH:7][N:6]=1)=O.Cl.[CH3:19][O:20][NH2:21]>C(O)C>[CH3:19][O:20][N:21]=[C:3]([C:5]1[C:10]([Cl:11])=[CH:9][C:8]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[CH:7][N:6]=1)[CH2:2][Br:1]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 1180715932-Bromo-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone

Product 1

HCID 1180716592-bromo-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone-O-methyloximeYield 84.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1.3 g of 2-bromo-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone in 10 ml of ethanol, 362 mg of methoxyamine hydrochloride was added, and the mixture was stirred at room temperature for 13 hours. After completion of the reaction, the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 0:100 to 5:95) to obtain 1.2 g of the desired product as a colorless oil.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-40d85bc262e84de38ac530141e6dc2dd
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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