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

HRID 2101374ノート

反応式

HRID 2101374 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c97784f20db546fab0d064a05cf3953d
出典データセット
uspto-grants-2009_08
特許番号
US07572808B2

反応ノート

読み込み中…