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

HRID 2101374노트

반응식

HRID 2101374 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c97784f20db546fab0d064a05cf3953d
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572808B2

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