Hydroxyamine hydrochloride → 1-(3-bromo-4-methoxyphenyl)-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-N-hydroxymethanimine

HRID 875198Notes

Reaction equation

HRID 875198 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][N:13]=2)=O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl.[NH2:24][OH:25]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:10]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][N:13]=2)=[N:24][OH:25])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 66887564(3-Bromo-4-methoxyphenyl)[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methanone

Product 1

HCID 1363312541-(3-bromo-4-methoxyphenyl)-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-N-hydroxymethanimineYield 97.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (3-bromo-4-methoxyphenyl)[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methanone (8.90 g, 22.5 mmol) and hydroxylamine hydrochloride (3.92 g, 56.3 mmol) in pyridine (60 mL) was stirred 2 h at 50° C. then overnight at room temperature. After removal of the solvent in vacuo, addition of water (50 mL) and extraction with ethyl acetate (3×40 mL), the combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified on silica gel to afford 1-(3-bromo-4-methoxyphenyl)-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-N-hydroxymethanimine [9.00 g, yield 88%; HPLC/MS: m/z=410 (M+H); log P(HCOOH)=3.37].

Workup

  1. customovernight
  2. customat room temperature
  3. customAfter removal of the solvent
  4. additionin vacuo, addition of water (50 mL) and extraction with ethyl acetate (3×40 mL)
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-1b0afe90437547a6aad1c1366ec5ebc8
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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