Ethyl chloroformate → 2-(2-ethoxycarbonylaminopropyl)-4-phenyl-1(2H)-isoquinolone

HRID 326023Notes

Reaction equation

HRID 326023 reaction equation
[NH2:1][CH:2]([CH3:21])[CH2:3][N:4]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:20].[C:22](Cl)(=[O:26])[O:23][CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:24]([O:23][C:22]([NH:1][CH:2]([CH3:21])[CH2:3][N:4]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:20])=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 132699402-(2-aminopropyl)-4-phenyl-1(2H)-isoquinolone

Product 1

HCID 132699422-(2-ethoxycarbonylaminopropyl)-4-phenyl-1(2H)-isoquinoloneYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.2 g of 2-(2-aminopropyl)-4-phenyl-1(2H)-isoquinolone, 2.7 g of ethyl chlorocarbonate, 4.1 g of potassium carbonate and 60 ml of ethanol were mixed and stirred at room temperature for 3 hours. The solvent was then distilled off, and the residue was extracted with dichloromethane. The crystals obtained by distilling off the solvent were recrystallized from ethanol to obtain 3 g (57% yield) of 2-(2-ethoxycarbonylaminopropyl)-4-phenyl-1(2H)-isoquinolone having a melting point of 182° C. as colorless prisms.

Workup

  1. distillationThe solvent was then distilled off
  2. extractionthe residue was extracted with dichloromethane
  3. customThe crystals obtained
  4. distillationby distilling off the solvent
  5. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-b8c5e07c55e040e3affde976c88d606e
Source dataset
uspto-grants-1984_04
Patent number
US04443607

Reaction notes

Loading…