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

HRID 54428

反応式

HRID 54428 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=O)[CH3:11])=[CH:4][CH:3]=1.[C:13]1(=[O:20])[CH2:18][CH2:17][CH2:16][C:15](=O)[CH2:14]1.C([O-])(=O)C.[NH4+:25]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:14]3[C:13](=[O:20])[CH2:18][CH2:17][CH2:16][C:15]=3[NH:25][C:10]([CH3:11])=[CH:9]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

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

生成物 1

HCID 199589244-(4-Chlorophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinolone収率 34%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

4-(4-Chlorophenyl)-3-butene-2-one (2.83 g), 1.3-cyclohexanedione (1.81 g), and ammonium acetate (2.60 g) were combined in ethanol (125 mL) and heated at reflux for 5.5 h. The solvent was evaporated, and the residue was taken up in water and extracted with ethyl acetate. The combined organic extracts were washed (water, brine), dried, and evaporated to yield a residue which was chromatographed, eluting with hexane:ethyl acetate (1:1) to yield the title compound as a pale yellow solid (1.46 g); mp 184°-187° C.; MS: 273 (M); NMR: 1.73 (s,3, CH3), 1.75-1.98 (m,2, CH2), 2.15 (m,2, CH2), 2.43 (t,2, J=6.0, CH2), 4.39 (d,1, J=4.7, CH), 4.58 (d,1,J=4.8, CH), 7.14 (d,2, J=8.4, Ar), 7.26 (d,2, J=8.4, Ar), 8.48 (s,1, NH); Analysis for C16H16ClNO: Calculated: C, 70.20; H, 5.89; N, 5.12; Found: C, 70.21; H, 5.67; N, 5.02.

後処理

  1. temperatureheated
  2. temperatureat reflux for 5.5 h
  3. customThe solvent was evaporated
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed (water, brine)
  6. customdried
  7. customevaporated
  8. customto yield a residue which
  9. customwas chromatographed
  10. washeluting with hexane:ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-24b806f6b1af4fd5b832f1988fcf1f78
出典データセット
uspto-grants-1997_04
特許番号
US05622964

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