Methanol → HCID 347963, compound

HRID 2388164Notes

Reaction equation

HRID 2388164 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].CO.[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=O)[CH2:12][CH3:13]>O>[C:15]1([C:11](=[N:2][OH:3])[CH2:12][CH3:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 71481-Phenyl-1-propanoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 347963HCID 347963, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydroxylamine hydrochloride (17.1 g, 246 mmol) and sodium acetate (20.2 g, 246 mmol) were added to 110 mL of methanol and the resulting white slurry was stirred at room temperature for 30 min. Propiophenone (30 g, 224 mmol) was added and the mixture was stirred at room temperature for 20 hours. Water (100 mL) was added and the mixture was stirred for 10 min. The product was extracted with EtOAc and the organic layer was washed with saturated NaHCO3 solution and dried over MgSO4. The solvent was evaporated in vacuo to give 32.4 g of the title compound. 1H NMR (CDCl3, 200 MHz): δ=9.21 (s, 1H), 7.60-7.72 (m, 2H), 7.38-7.50 (m, 3H), 2.91 (q, 2H, J=7.8 Hz), 1.23 (t, 3H, J=7.4 Hz).

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hours
  2. stirringthe mixture was stirred for 10 min
  3. extractionThe product was extracted with EtOAc
  4. washthe organic layer was washed with saturated NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-857e09da722845cbb9980a5ed8d18a86
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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