Dimethylformamide → 3-Phenoxy-6,7-dimethylquinoline

HRID 374475

반응식

HRID 374475 반응식
OC1C=N[C:5]2[C:10](C=1)=[CH:9][C:8](OC)=[C:7]([O:14][CH3:15])[CH:6]=2.F[B-](F)(F)F.[C:21](#N)C.O(C1C=N[C:34]2[C:39]([CH:40]=1)=[CH:38][C:37](OC)=[C:36](OC)[CH:35]=2)C1C=CC=CC=1.C[N:46]([CH:48]=O)[CH3:47]>CCOC(C)=O>[O:14]([C:15]1[CH:48]=[N:46][C:47]2[C:36]([CH:35]=1)=[CH:37][C:38]([CH3:21])=[C:39]([CH3:34])[CH:40]=2)[C:7]1[CH:6]=[CH:5][CH:10]=[CH:9][CH:8]=1

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 6342AcetonitrileHCID 26255TetrafluoroborateHCID 100587666,7-Dimethoxyquinolin-3-olHCID 187885233-Phenoxy-6.7-dimethoxyquinoline

생성물 1

HCID 187885123-Phenoxy-6,7-dimethylquinoline

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of Nail (1.2g; 60% disp in oil) in DMF (3 ml) is added 3-hydroxy-6.7-dimethoxyquinoline (150 mg; 0.73 tool) and the reaction mixture is allowed to stir for 30 minutes at room temperature. To this is added the tetrafluoroborate salt of chlorobenzene manganese tricarbonyl complex (prepared by J.O.C. 24: 1991;7092) (183 mg) and stirred for 3 hours. To this is added 20 ml of acetonitrile and stirred overnight. The reaction mixture is dissolved in EtOAc: brine and extracted 2× with EtOAc, washed with water 2×, washed with brine, dried (MgSO4) and concentrated in vacuo to obtain a material which is purified by FPLC using 1% methanol: chloroform to obtain a solid which NMR indicates to be 3-phenoxy-6.7-dimethoxyquinoline. The hydrochloride salt is then prepared in the usual manner m.p. 224-226).

후처리

  1. stirringstirred for 3 hours
  2. stirringstirred overnight
  3. extractionbrine and extracted 2× with EtOAc
  4. washwashed with water 2×
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto obtain a material which
  9. customis purified by FPLC
  10. customchloroform to obtain a solid which NMR

출처 및 근거

ORD 기록
ord-ab14419644814ee3bb8e86fbe06154d2
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05480883

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