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

HRID 54429ノート

反応式

HRID 54429 の反応式
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11](=O)[CH3:12])[CH:6]=[CH:7][CH:8]=1.[C:16]1(=[O:23])[CH2:21][CH2:20][CH2:19][C:18](=O)[CH2:17]1.C([O-])(=O)C.[NH4+:28]>C(O)C>[CH3:12][C:11]1[NH:28][C:18]2[CH2:19][CH2:20][CH2:21][C:16](=[O:23])[C:17]=2[CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:15])([F:14])[F:1])[CH:4]=2)[CH:10]=1

参加物

5

反応物 3

HCID 104341,3-CyclohexanedioneHCID 1449341-[3-(Trifluoromethyl)phenyl]but-1-en-3-oneHCID 517165Ammonium Acetate

生成物 1

HCID 199589122-Methyl-4-(3-trifluoromethylphenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone収率 39.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 4-(3-trifluoromethylphenyl)-3-butene-2-one (4.9 g), 1,3-cyclohexanedione (2.68 g), ammonium acetate (2.65 g) and 75 mL of ethanol were heated at reflux for eight hours 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 yield a yellow solid. Recrystallization from ethyl acetate provided the title compound (2.8 g) as an off-white solid; mp 184°-185° C.; NMR: 1.74 (s,3, CH3), 1.87-1.98 (m,2, CH2), 2.13-2.19 (m,2, CH2), 2.42-2.49 (m,2, CH2), 4.50 (d,1, J=4.9, CH), 4.63 (d,1, J=4.9, CH), 7.45 (s,4, Ar), 8.53 (s,1, NH); (CI, CH4) MS: m/z=308(M+1). Analysis for C17H16F3NO: Calculated: C, 66.44; H, 5.25; N, 4.56; Found: C, 65.90; H, 5.33; N, 4.43.

後処理

  1. temperaturewere heated
  2. temperatureat reflux for eight hours
  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 yield a yellow solid
  9. customRecrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-07b7e2ca3f694977a7cdc93679f65c63
出典データセット
uspto-grants-1997_04
特許番号
US05622964

反応ノート

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