7-Methylquinoline → 7-Methyl-2-phenylquinoline

HRID 230244

반응식

HRID 230244 반응식
[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

참가 물질

4

반응물 2

HCID 119277-MethylquinolineHCID 178506676HCID 178506676, 화합물

생성물 1

HCID 2877157-Methyl-2-phenylquinoline

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e755b54428044289aaa7fd933ec31626
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566721B2

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