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

HRID 1256944
Notes
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Reaction equation

HRID 1256944 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-8b814db719d3473c9dd6c31abd5e08e4
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08461329B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes