Hydroxyamine hydrochloride → 3,5-Difluoro-4-((hydroxyimino)methyl)benzonitrile
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
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
- concentrationthen concentrated in vacuo
- 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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