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

HRID 706164ノート

反応式

HRID 706164 の反応式
[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]

参加物

10

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 62652Cuprous chloride触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3e3920ed90014d41a9dcc2dc007e03fe
出典データセット
uspto-grants-2015_11
特許番号
US09174976B2

反応ノート

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