Methyl iodide → 6-chloro-2-dimethylamino-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750128ノート

反応式

HRID 750128 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]([NH:23][CH3:24])[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:21])=[CH:10][CH:9]=2)=[O:4].[C:25](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([N:23]([CH3:25])[CH3:24])[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:21])=[CH:10][CH:9]=2)=[O:4]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 101259456-chloro-2-methylamino-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

生成物 1

HCID 102869016-chloro-2-dimethylamino-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester収率 56.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 6-chloro-2-methylamino-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (800 mg), potassium carbonate (400 mg), methyl iodide (20 ml) and DMF (20 ml) was stirred at 80° C. for 3 days. The reaction mixture was concentrated, and ethyl acetate was added to the obtained residue. The mixture was washed with water and brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) and crystallized from isopropyl ether to give the title compound (469 mg) as colorless crystals.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additionethyl acetate was added to the obtained residue
  3. washThe mixture was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)
  7. customcrystallized from isopropyl ether

出典と根拠

ORDレコード
ord-4151e229453642639bc4cb91592dd12f
出典データセット
uspto-grants-2008_07
特許番号
US07402595B2

反応ノート

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