Chloroacetone → 7-Chloro-2-methylimidazo[2,1-a]isoquinoline

HRID 649146Notes

Reaction equation

HRID 649146 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[C:7]2[NH2:12].Cl[CH2:14][C:15](=O)[CH3:16].C(=O)(O)[O-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]1[CH:14]=[C:15]([CH3:16])[N:12]=[C:7]12

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 516892Sodium BicarbonateHCID 138218255-Chloroisoquinolin-1-amine

Product 1

HCID 138218267-Chloro-2-methylimidazo[2,1-a]isoquinolineYield 82.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-chloro-1-aminoisoquinoline (2.8 g), chloroacetone (5.4 g) and sodium bicarbonate (7.6 g) in anhydrous ethanol (35 ml) was heated at 60° C. for 16 hours and filtered by suction. The filtrate was evaporated in vacuo and the residual solid was washed with ethanol to give 7-chloro-2-methylimidazo[2,1-a]isoquinoline (2.8 g).

Workup

  1. filtrationfiltered by suction
  2. customThe filtrate was evaporated in vacuo
  3. washthe residual solid was washed with ethanol

Sources & evidence

ORD record
ord-fc89981060024128972547fa25e9b8cb
Source dataset
uspto-grants-1988_04
Patent number
US04738967

Reaction notes

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