Hydrochloric Acid → 4-Hydroxy-8-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester

HRID 409233노트

반응식

HRID 409233 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[CH:10][C:9]=2I)=[O:4].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C.Cl>Cl[Cu].O.C(OCC)(=O)C.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[CH:10][C:9]=2[O:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=1)=[O:4]

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 90154-MethoxyphenolHCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 67110147Methyl 4-hydroxy-8-iodoisoquinoline-3-carboxylate

생성물 1

HCID 671102494-Hydroxy-8-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester수율 10.3%

시약·촉매·용매 4

HCID 62652Cuprous chloride촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 4-Hydroxy-8-iodo-isoquinoline-3-carboxylic acid methyl ester (7 mmol, 2.3 g), 4-methoxy-phenol (35 mmol, 4.39 g), Cs2CO3 (35 mmol, 11.42 g), 2,2,6,6-tetramethyl-heptane-3,5-dione (2.8 mmol, 0.59 mL), CuCl (7 mmol, 0.70 g), and anhydrous DMF (42 mL) was refluxed under nitrogen with stirring for 15 min. before it was poured into ethyl acetate (700 mL). Water (700 mL) and 5 N hydrochloric acid (5 mL) were added and the mixture was stirred for 15 min. The organic phase was then separated and washed with water (2×700 mL) before it was dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel using hexanes:EtOAc=75:25 as the eluent gave the title compound as a tan solid (234 mg); MS-(+)-ion: M+1=326.4.

후처리

  1. temperaturewas refluxed under nitrogen
  2. stirringthe mixture was stirred for 15 min
  3. customThe organic phase was then separated
  4. washwashed with water (2×700 mL) before it
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash column chromatography on silica gel

출처 및 근거

ORD 기록
ord-1e22b5f676ba4c56bab1e04ae14ae284
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759373B2

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