Ethanol → 4-(3-Chlorophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinolone

HRID 54431

반응식

HRID 54431 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](C=CC(=O)C)=[CH:4][CH:3]=1.[C:13]1(=[O:20])[CH2:18][CH2:17][CH2:16][C:15](=O)[CH2:14]1.[C:21]([O-])(=O)[CH3:22].[NH4+:25].[CH2:26](O)[CH3:27]>>[Cl:1][C:2]1[CH:7]=[C:6]([CH:26]2[C:14]3[C:13](=[O:20])[CH2:18][CH2:17][CH2:16][C:15]=3[NH:25][C:21]([CH3:22])=[CH:27]2)[CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 4

HCID 702EthanolHCID 104341,3-CyclohexanedioneHCID 981834-ChlorobenzalacetoneHCID 517165Ammonium Acetate

생성물 1

HCID 199589214-(3-Chlorophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinolone

실험 절차

A mixture of 4-(4-chlorophenyl)-3-butene-2-one (5.0 g), 1,3-cyclohexanedione (3.24 g), ammonium acetate (3.20 g) and 90 mL of ethanol were heated at reflux overnight and then cooled to room temperature. The solvent was evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was dried, filtered, and evaporated to obtain a yellow solid. Recrystallization from ethanol provided the title compound as a yellow solid (3.0 g); mp 201°-203° C.; NMR: 1.73 (s,3, CH3), 1.87-1.98 (m,2, CH2), 2.13-2.17 (m,2, CH2), 2.43-2.49 (m,2, CH2), 4.40 (d,1, J=4.9, CH), 4.60 (d,1, J=4.9, CH), 7.09-7.25 (m,4, Ar), 8.50 (s,1, NH); (CI, CH4) MS: m/z=274(M+1). Analysis for C16H16ClNO.0.15 H2O: Calculated: C, 69.51; H, 5.94; N, 5.07; Found: C, 69.47; H, 6.03; N, 4.91.

후처리

  1. temperaturewere heated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between water and ethyl acetate
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customevaporated
  8. customto obtain a yellow solid
  9. customRecrystallization from ethanol

출처 및 근거

ORD 기록
ord-fb6dfcb9be9c41c0b751a04f63012648
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622964

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