7-Methylquinoline → 7-Methyl-2-phenylquinoline

HRID 422594

反応式

HRID 422594 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 (10mL), 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 rt 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 7 d. 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).

後処理

  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 7 d
  11. customThe solvent is evaporated
  12. dissolutionthe residue is dissolved
  13. temperaturein warm (≈50° C.) EtOAc/hexanes
  14. filtrationfiltered
  15. temperaturewarm
  16. concentrationThe filtrate is concentrated
  17. customdried in vacuo

出典と根拠

ORDレコード
ord-59d911325e54456cbe478eea03a5300e
出典データセット
uspto-grants-2012_01
特許番号
US08101613B2

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