Hydroxyamine hydrochloride → 3,5-Difluoro-4-((hydroxyimino)methyl)benzonitrile

HRID 929912Notes

Reaction equation

HRID 929912 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:12])[C:9]=1[CH:10]=O)[C:5]#[N:6].Cl.[NH2:14][OH:15].C([O-])(=O)C.[K+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:12])[C:9]=1[CH:10]=[N:14][OH:15])[C:5]#[N:6]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517044Potassium AcetateHCID 162182563,5-Difluoro-4-formylbenzonitrile

Product 1

HCID 900148513,5-Difluoro-4-((hydroxyimino)methyl)benzonitrileYield 23.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3,5-difluoro-4-formylbenzonitrile (500 mg, 3.0 mmol), hydroxylamine hydrochloride (207 mg, 3.0 mmol) and potassium acetate (586 mg, 6.0 mmol) in methanol (10 mL) was heated to 60° C. for 1 h then concentrated in vacuo and purified by column chromatography (eluent: DCM) to afford 3,5-difluoro-4-((hydroxyimino)methyl)benzonitrile (130 mg, 0.7 mmol) as a white solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. custompurified by column chromatography (eluent: DCM)

Sources & evidence

ORD record
ord-d6c74245b79441fd9cbd77aeeca64ec0
Source dataset
uspto-grants-2016_03
Patent number
US09296725B2

Reaction notes

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