7-Methylquinoline → 7-Methyl-2-phenylquinoline

HRID 230244

反応式

HRID 230244 の反応式
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:12]1([Li])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:9]2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 119277-MethylquinolineHCID 178506676HCID 178506676、化合物

生成物 1

HCID 2877157-Methyl-2-phenylquinoline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 7-methylquinoline (1.63 g, 11.4 mmol) in dry THF (10 mL), cooled by ice/water, was added phenyllithium (1.9 M in cyclohexane/ether 70/30, 6.0 mL, 11.4 mmol) dropwise over 5 min. After 15 min, the cooling bath was removed, and the solution was stirred at ambient temperature for 5 h. The reaction was quenched by adding MeOH, and stirring was continued overnight. Water was added, the mixture was extracted with EtOAc (3×35 mL), and the combined extracts were dried over MgSO4. The drying agent was filtered off, and air was bubbled into the solution for 7 d. The solvent was evaporated; the residue was dissolved in warm (≈50° C.) EtOAc/hexanes and filtered warm. The filtrate was concentrated and dried in vacuo, giving the crude title compound that was used directly for the next step. A sample was purified further by chromatography on silica gel (Jones Flashmaster, eluting with hexanes:EtOAc 3:1→2:1→1:1). 1H NMR (CDCl3, 400 MHz): δ=2.58 (s, 3H), 7.31 (d, J=3.7 Hz, 1H), 7.36-7.49 (m, 1H), 7.52 (t, J=8.0 Hz, 2H), 7.72 (d, J=8.2 Hz, 1H), 7.82 (d, J=8.2 Hz, 1H), 7.96 (s, 1H), 8.16 (t, J=8.0 Hz, 2H). MS (ES+): m/z 220.3 (100) [MH+]. HPLC: tR=2.7 min (Platform II, nonpolar—5 min).

後処理

  1. customthe cooling bath was removed
  2. customThe reaction was quenched
  3. additionby adding MeOH
  4. stirringstirring
  5. waitwas continued overnight
  6. additionWater was added
  7. extractionthe mixture was extracted with EtOAc (3×35 mL)
  8. dry with materialthe combined extracts were dried over MgSO4
  9. filtrationThe drying agent was filtered off
  10. customair was bubbled into the solution for 7 d
  11. customThe solvent was evaporated
  12. dissolutionthe residue was dissolved
  13. temperaturein warm (≈50° C.) EtOAc/hexanes
  14. filtrationfiltered
  15. temperaturewarm
  16. concentrationThe filtrate was concentrated
  17. customdried in vacuo

出典と根拠

ORDレコード
ord-e755b54428044289aaa7fd933ec31626
出典データセット
uspto-grants-2009_07
特許番号
US07566721B2

関連ノート

読み込み中…