Hydroxyamine hydrochloride → HCID 86246798, compound

HRID 2113455Notes

Reaction equation

HRID 2113455 reaction equation
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[CH:4]=O.Cl.[NH2:13][OH:14].C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[CH:4]=[N:13][OH:14]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 27735092-Chloro-3,6-difluorobenzaldehyde

Product 1

HCID 86246798HCID 86246798, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloro-3,6-difluoro-benzaldehyde (16.5 g, 93 mmol) in ethanol (80 ml) was treated with hydroxylamine HCl (7.80 g, 112 mmol) and sodium acetate (9.20 g, 112 mmol). The mixture was heated under reflux for 16 h, then the solvent was evaporated, and the residue stirred with water. The precipitate was filtered and dried to afford 2-chloro-3,6-difluoro-benzaldehyde oxime. It was dissolved in acetic anhydride (140 ml) and refluxed for 16 h, then the mixture was evaporated to afford 2-chloro-3,6-difluoro-benzonitrile as a light brown liquid (10.6 g, 65%). In analogy to example 5a, this compound was reacted with 4-methylimidazole and potassium carbonate for 20 h at 90° C. Aqueous workup, extraction with Ethyl acetate followed by chromatography (SiO2, dichloromethane:methanol=100:0 to 97:3) afforded the title compound as a white solid (yield: 6%). MS: m/e=336.1 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 16 h
  3. customthe solvent was evaporated
  4. filtrationThe precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-f2b827448ab24763ac42d186770d8246
Source dataset
uspto-grants-2008_10
Patent number
US07432256B2

Reaction notes

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