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

HRID 2209543ノート

反応式

HRID 2209543 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[C:11]1(=[O:18])[CH2:16][CH2:15][CH2:14][C:13](=O)[CH2:12]1.[C:19]([O-])(=O)C.[NH4+].C(O)(=O)C.[NH:28]1[CH2:32][CH2:31]CC1>C(O)C.CC(C)=O>[CH3:19][C:32]1[NH:28][C:13]2[CH2:14][CH2:15][CH2:16][C:11](=[O:18])[C:12]=2[CH:5]([C:4]2[CH:7]=[CH:8][C:9]([F:10])=[C:2]([Cl:1])[CH:3]=2)[CH:31]=1

参加物

7

反応物 4

HCID 104341,3-CyclohexanedioneHCID 517165Ammonium AcetateHCID 5938663-Chloro-4-fluorobenzaldehydeHCID 11040738Pyrrolidine, acetate

生成物 1

HCID 199589372-Methyl-4-(3-chloro-4-fluorophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone収率 2.8%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 702Ethanol溶媒2 回

反応条件

温度
50 °C

実験手順

A mixture of 3-chloro-4-fluoro benzaldehyde (2.7 g), 1,3-cyclohexanedione (1.99 g) and 47 mL of ethanol were heated at 50° C. overnight and then cooled to room temperature. Acetone (1.18 g), ammonium acetate (1.97 g) and a premixed solution of pyrrolidine acetate (20.4 mmole) in 5 mL of ethanol were added and heated at 70° C. for three hours and then cooled to room temperature. The solvent was evaporated in vacuo and the residue was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography (eluant: ether/hexane; 9.0/1.0) over silica gel provided the title compound 0.140 g as a yellow solid, m.p. 164°-167° C. 1H-NMR (300 MHz, d6-DMSO): 1.74(s, 3H,CH3), 1.81-1.88(m, 2H, CH2) 2.15-2.19(m,2H, CH2), 2.41-2.48(m,2H,CH2), 4.41(d,1H, J=4.8 Hz, CH), 4.60(d, 1H, J=4.8(Hz,CH), 7.10-7.28(m,3H, aromatic), 8.54(s, 1H, NH); MS (Cl, CH4): 292 (M+1): Analysis for C16H15ClFNO: Calculated: C; 65.87; H; 5.18; N; 4.80: Found: C; 65.67; H; 5.50; N; 4.48.

後処理

  1. temperaturecooled to room temperature
  2. temperatureheated at 70° C. for three hours
  3. temperaturecooled to room temperature
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was partitioned between water and ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-deda93e3d2f94b4facad0997089cfcc9
出典データセット
uspto-grants-1995_10
特許番号
US05455253

反応ノート

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