Methanol → 4-Hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid butyl ester

HRID 250394

반응식

HRID 250394 반응식
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](Br)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].C([O-])(=O)C.[Na+].CO>[Pd].C(OCC)(=O)C>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 3

HCID 887MethanolHCID 517045Sodium AcetateHCID 86595463Butyl 1-bromo-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

생성물 1

HCID 667129514-Hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid butyl ester수율 77.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 208 mg of 1-Bromo-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid butyl ester (0.5 mmol), 49 mg of sodium acetate (0.6 mmol), 50 mg of 10 wt % palladium on charcoal, 10 ml of methanol, and 5 ml of ethyl acetate was stirred under hydrogen at 1 atm for 15 h. Then the mixture was filtered by suction through a pad of celite and was concentrated in vacuo. The residue was partitioned between 2 ml of half concentrated aqueous bicarbonate solution and 8 ml of ethyl acetate. The organic phase was dried over MgSO4. Evaporation in vacuo gave 130 mg of the title compound; 1H NMR (CDCl3): δ=11.89 (bs, 1H), 8.61 (s, 1H), 8.36 (d, 1H), 7.10 to 7.53 (m, 7H), 4.49 (t, 2H), 1.87 (m, 2H), 1.47 (m, 2H), 0.98 (t, 3H).

후처리

  1. filtrationThen the mixture was filtered by suction through a pad of celite
  2. concentrationwas concentrated in vacuo
  3. customThe residue was partitioned between 2 ml of half concentrated aqueous bicarbonate solution and 8 ml of ethyl acetate
  4. dry with materialThe organic phase was dried over MgSO4
  5. customEvaporation in vacuo

출처 및 근거

ORD 기록
ord-388d2cab882148c4abf84bf964a70fc6
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863292B2

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