Ethanol → 2-Methyl-4-(4-methylphenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

HRID 2209514

반응식

HRID 2209514 반응식
[CH3:1][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>CCOCC.CCCCCC.C(OCC)(=O)C>[CH3:11][C:10]1[NH:25][C:15]2[CH2:16][CH2:17][CH2:18][C:13](=[O:20])[C:14]=2[CH:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:9]=1

참가 물질

7

반응물 4

HCID 702EthanolHCID 104341,3-CyclohexanedioneHCID 1073884-(4-Methylphenyl)-3-buten-2-oneHCID 517165Ammonium Acetate

생성물 1

HCID 199589302-Methyl-4-(4-methylphenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone수율 25.3%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 21226206Ethyl acetate hexane용매

실험 절차

A mixture of 4-(4-methyphenyl)-3-butene-2-one (5.0 g), 1,3-cyclohexanedione (3.66 g), ammonium acetate (3.61 g) and 100 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 an amber oil. Chromatography, with hexane:ethyl acetate (1:1) as the eluent, and trituration from ether provided the title compound as an off-white solid (2.0 g); mp 196°-198° C.; NMR: 1.73 (s,3, CH3), 1.87-1.98 (m,2, CH2), 2.14-2.16 (m,2, CH2), 2.22 (s,3, CH3), 2.43-2.49 (m,2, CH2), 4.34 (d,1, CH), 4.57 (d,1, CH), 7.01 (s,4, Ar), 8.40 (s,1, NH); (CI, CH4) MS: m/z=254(M+1). Analysis for C17H19NO: Calculated C, 80.60; H, 7.56; N, 5.53; Found: C, 80.24; H, 7.68; N, 5.36.

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 an amber oil

출처 및 근거

ORD 기록
ord-98b6075338e347a99060ffceb9a3fdce
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05455253

연결된 노트

불러오는 중…