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

HRID 54456

반응식

HRID 54456 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]1(=[O:17])[CH2:15][CH2:14][CH2:13][C:12](=O)[CH2:11]1.[C:18]([O-])(=O)C.[NH4+].C(O)(=O)C.[NH:27]1[CH2:31][CH2:30]CC1>C(O)C.CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:11]3[C:10](=[O:17])[CH2:15][CH2:14][CH2:13][C:12]=3[NH:27][C:31]([CH3:30])=[CH:18]2)[CH:7]=[CH:8][CH:9]=1

참가 물질

7

반응물 4

HCID 104341,3-CyclohexanedioneHCID 680093-FluorobenzaldehydeHCID 517165Ammonium AcetateHCID 11040738Pyrrolidine, acetate

생성물 1

HCID 199589284-(3-Fluorophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinolone

시약·촉매·용매 2

HCID 180Acetone용매HCID 702Ethanol용매2회

반응 조건

온도
70 °C

실험 절차

A mixture of 3-fluorobenzaldehyde (7.0 1,3-cyclohexanedione (6.61 g) and ethanol (150 mL) was heated at 70° C. overnight and then cooled to room temperature. Acetone (3.93 g), ammonium acetate (6.52 g) and a solution of pyrrolidine acetate (9.83 g) in ethanol (10 mL) was added and heated at 70° C. for three hours and then cooled to room temperature. The solvent was removed and the residue was partitioned between water and ethyl acetate. The organic layer was dried, filtered, and concentrated in vacuo to obtain an amber oil. Chromatography (methylene chloride/ethyl acetate; 9.0/1.0) and recrystallization from ethanol provided the title compound (0.12 g) as a white solid, mp 216°-218° C.; NMR: 1.73 (s,3, CH3), 1.78-1.90 (m,2, CH2), 2.14-2.19 (m,2, CH2), 2.41-2.46 (m,2, CH2), 4.42 (d,1, 4.8, CH), 4.61 (d,1, J=4.8, CH) 6.86-7.00 (m,3, Ar), 7.25 (m,1, Ar), 8.49 (s,1, NH); (CI, CH4) MS: m/z=258(M+1). Analysis for C16H16FNO: Calculated: C, 74.69; H, 6.27; N, 5.44; Found: C, 74.39; H, 6.30; N, 5.35.

후처리

  1. temperaturecooled to room temperature
  2. temperatureheated at 70° C. for three hours
  3. temperaturecooled to room temperature
  4. customThe solvent was removed
  5. customthe residue was partitioned between water and ethyl acetate
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto obtain an amber oil
  10. customChromatography (methylene chloride/ethyl acetate; 9.0/1.0) and recrystallization from ethanol

출처 및 근거

ORD 기록
ord-8c00d6b25bca4d35beb312c3151c44e8
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622964

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