Ammonium Acetate → 4-(4-chloro-phenyl)-6-methyl-1H-pyridin-2-one

HRID 2101374Notes

Reaction equation

HRID 2101374 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10](=[O:12])C)=[CH:4][CH:3]=1.[Cl-].C(OC(=O)C[N+:19]1[CH:24]=[CH:23]C=CC=1)C.[C:26]([O-])(=O)C.[NH4+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:26]=[C:24]([CH3:23])[NH:19][C:10](=[O:12])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 7365724-(4-Chlorophenyl)-3-buten-2-oneHCID 111381401-(2-Ethoxy-2-oxoethyl)pyridin-1-ium chloride

Product 1

HCID 574686404-(4-chloro-phenyl)-6-methyl-1H-pyridin-2-oneYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of (E)-4-(4-chlorophenyl)but-3-en-2-one (5.42 g, 30 mmol, Aldrich Chemical Co.), 1-(2-ethoxy-2-oxoethyl)pyridinium chloride (6.05 g, 30 mmol) (prepared according to the procedure described in WO 94/04502) and ammonium acetate (46.3 g, 0.6 mol) in ethanol (150 mL) was stirred at room temperature for 15 min, then at reflux for 4 h. The reaction mixture was allowed to cool and stand at room temperature overnight. The resulting precipitate was collected by filtration, and the collected solid was washed with ethanol, then water, and dried in a vacuum oven at 45° C. for 16 h to afford 3.1 g (47%) of the title compound as an off-white solid. HPLC/MS: retention time=2.86 min, [M+H]+=220.3.

Workup

  1. customprepared
  2. temperatureat reflux for 4 h
  3. temperatureto cool
  4. waitstand at room temperature overnight
  5. filtrationThe resulting precipitate was collected by filtration
  6. washthe collected solid was washed with ethanol
  7. dry with materialwater, and dried in a vacuum oven at 45° C. for 16 h

Sources & evidence

ORD record
ord-c97784f20db546fab0d064a05cf3953d
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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