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Ethyl Acetate → Methyl 1-(4-{[2-(4-chlorophenyl)ethyl]carbamoyl}phenoxy)isoquinoline-4-carboxylate

HRID 1256944
ノート
印刷プレビュー

反応式

HRID 1256944 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[CH3:20][O:21][C:22]([C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](Cl)=[N:26][CH:25]=1)=[O:23].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]([C:12]2[CH:13]=[CH:14][C:15]([O:18][C:27]3[C:28]4[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:24]([C:22]([O:21][CH3:20])=[O:23])=[CH:25][N:26]=3)=[CH:16][CH:17]=2)=[O:19])=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 3338790Methyl 1-chloroisoquinoline-4-carboxylateHCID 60628097N-(4-chlorophenethyl)-4-hydroxybenzamide

生成物 1

HCID 67007699Methyl 1-(4-{[2-(4-chlorophenyl)ethyl]carbamoyl}phenoxy)isoquinoline-4-carboxylate収率 84.9%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
60 °C

実験手順

A suspension of N-[2-(4-chlorophenyl)ethyl]-4-hydroxy benzamide (605 mg) and 1-chloro-isoquinoline-4-carboxylic acid methyl ester (443 mg) and potassium carbonate (332 mg) in DMF (4 ml) was stirred at 60° C. for two hours. Ethyl acetate was added thereto, and the reaction solution was washed with water, and then washed with a saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate, and then evaporated under reduced pressure to remove the solvent. The resulting crude product was purified by column chromatography (NH type silica gel, chloroform/n-hexane=50 to 80%) to give methyl 1-(4-{[2-(4-chlorophenyl)ethyl]carbamoyl}phenoxy)isoquinoline-4-carboxylate (782 mg) as a colorless solid.

後処理

  1. washthe reaction solution was washed with water
  2. washwashed with a saturated saline solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto remove the solvent
  6. customThe resulting crude product was purified by column chromatography (NH type silica gel, chloroform/n-hexane=50 to 80%)

出典と根拠

ORDレコード
ord-8b814db719d3473c9dd6c31abd5e08e4
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08461329B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート