Hydroxyamine hydrochloride → 5-Fluorosalicylaldoxime

HRID 645556Notes

Reaction equation

HRID 645556 reaction equation
[OH2:1].O.O.C([O-])(=O)C.[Na+].[F:9][C:10]1[CH:11]=[CH:12][C:13]([OH:18])=[C:14]([CH:17]=1)[CH:15]=O.[NH2:19]O.Cl>O.C(O)C>[F:9][C:10]1[CH:11]=[CH:12][C:13]([OH:18])=[C:14]([CH:17]=1)[CH:15]=[N:19][OH:1]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 27373285-FluorosalicylaldehydeHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 1363350925-FluorosalicylaldoximeYield 83.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium acetate trihydrate (1.94 g, 14.28 mmol) in H2O (8 mL) was added to a warm solution of 5-fluoro-2-hydroxy-benzaldehyde (1.0 g, 7.14 mmol) and NH2OH HCl (992 mg, 14.28 mmol) in 80% ethanol (30 mL). The reaction mixture was refluxed for 3 hr. Removal of ethanol, the mixture was cooled to rt, collected the precipitate and washed with water, dried to afford the title compound (920 mg, 83%). MS (DCI/NH3) m/z 217 (M+62)+. 1H NMR (500 MHz, DMSO-d6) δ ppm 6.89 (dd, J=9.15, 4.88 Hz, 1H) 7.07 (td, J=8.54, 3.05 Hz, 1H) 7.29 (dd, J=9.46, 3.05 Hz, 1H) 8.30 (s, 1H) 10.02 (brs, 1H) 11.46 (brs, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hr
  2. customRemoval of ethanol
  3. customcollected the precipitate
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-0d5526b86f0a49fca3e129ccbad8ccfc
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Reaction notes

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