Water → 3-(1-(Hydroxyimino)ethyl)benzoic acid

HRID 467501Notes

Reaction equation

HRID 467501 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])(=O)[CH3:2].Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+].O>C(O)C>[OH:15][N:14]=[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 2203243-Acetylbenzoic acidHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 766866363-(1-(Hydroxyimino)ethyl)benzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Acetylbenzoic acid (10.0 g, 60.9 mmol), hydroxylamine hydrochloride (33.9 g, 487.4 mmol) and sodium acetate (45.0 g, 548.3 mmol) were suspended in ethanol (115 mL) and water (115 mL) and the mixture heated at reflux for 30 minutes. The solvents were removed under reduced pressure, and the residue was triturated with water. The resulting precipitate was isolated by filtration and dried in vacuo to give the sub-title compound as a white solid (10.34 g, 95% yield). 1H NMR (400 MHz, DMSO) δ 2.18 (s, 3H), 7.52 (t, 1H), 7.88 (dd, 1H), 7.91-7.95 (m, 1H), 8.22 (s, 1H), 11.36 (s, 1H) and 12.86 (s, 1H); MS (ES+) 180.3.

Workup

  1. temperatureat reflux for 30 minutes
  2. customThe solvents were removed under reduced pressure
  3. customthe residue was triturated with water
  4. customThe resulting precipitate was isolated by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0ef1e2ca5c914220b5abc45c50489397
Source dataset
uspto-grants-2014_01
Patent number
US08623869B2

Reaction notes

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