7-Methylquinoline → 7-Methyl-2-phenylquinoline

HRID 386158

반응식

HRID 386158 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

반응 조건

온도
50 °C

실험 절차

To a solution of 7-methylquinoline (1.63 g, 11.4 mmol) in dry THF (10 mL), cooled by ice/water, is added phenyllithium (1.9M in cyclohexane/ether 70/30, 6.0 mL, 11.4 mmol) dropwise over 5 min. After 15 min, the cooling bath is removed, and the solution is stirred at it for 5 h. The reaction is quenched by adding MeOH, and stirring is continued overnight. Water is added, the mixture is extracted with EtOAc (3×35 mL), and the combined extracts are dried over MgSO4. The drying agent is filtered off, and air is bubbled into the solution for 7d. The solvent is evaporated; the residue is dissolved in warm (≈50° C.) EtOAc/hexanes and filtered warm. The filtrate is concentrated and dried in vacuo to obtain the crude title compound that is used directly for the next step. Further purification is possible 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 is removed
  2. customThe reaction is quenched
  3. additionby adding MeOH
  4. stirringstirring
  5. waitis continued overnight
  6. additionWater is added
  7. extractionthe mixture is extracted with EtOAc (3×35 mL)
  8. dry with materialthe combined extracts are dried over MgSO4
  9. filtrationThe drying agent is filtered off
  10. customair is bubbled into the solution for 7d
  11. customThe solvent is evaporated
  12. dissolutionthe residue is dissolved
  13. filtrationfiltered
  14. temperaturewarm
  15. concentrationThe filtrate is concentrated
  16. customdried in vacuo

출처 및 근거

ORD 기록
ord-27b61ed03c844265ba8c39ad6320569d
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367826B2

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