Hydroxyamine hydrochloride → (NE)-N-[[2-fluoro-5-(trifluoromethoxy)phenyl]methylidene]hydroxylamine

HRID 1786219Notes

Reaction equation

HRID 1786219 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:16][OH:17].C([O-])(=O)C.[Na+]>C(O)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1/[CH:4]=[N:16]/[OH:17]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 27833242-Fluoro-5-(trifluoromethoxy)benzaldehyde

Product 1

HCID 87441576(NE)-N-[[2-fluoro-5-(trifluoromethoxy)phenyl]methylidene]hydroxylamineYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-fluoro-5-trifluoromethoxy-benzaldehyde (9.78 g, 47 mmol) in ethanol (50 mL) was treated with hydroxylamine HCl (3.59 g, 52 mmol) and sodium acetate (4.27 g, 52 mmol). The resulting mixture was heated under reflux for 2 h. The solvent was then evaporated and the residue stirred with water (50 mL). The precipitate was filtered off, dried and chromatographed (SiO2, heptanes:ethyl acetate=100:0 to 80:2) to afford the title compound (9.21 g, 88%) as a white solid. MS: m/e=223.0 [M]+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 2 h
  3. customThe solvent was then evaporated
  4. filtrationThe precipitate was filtered off
  5. customdried
  6. customchromatographed (SiO2, heptanes:ethyl acetate=100:0 to 80:2)

Sources & evidence

ORD record
ord-a3211107e5894fde95e55084ef018fbe
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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