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

HRID 54429노트

반응식

HRID 54429 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-07b7e2ca3f694977a7cdc93679f65c63
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622964

반응 노트

불러오는 중…