Sodium Bicarbonate → 7-Chloro-3-ethoxycarbonyl-2-methylimidazo[2,1-a]isoquinoline

HRID 649166Notes

Reaction equation

HRID 649166 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:13]([CH:16](Br)[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=O)[CH3:14].C(=O)(O)[O-].[Na+]>C(O)C>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[CH:4][N:3]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:13]([CH3:14])[N:1]=[C:2]12

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11206579Ethyl 2-bromo-3-oxobutanoateHCID 138218255-Chloroisoquinolin-1-amine

Product 1

HCID 138218627-Chloro-3-ethoxycarbonyl-2-methylimidazo[2,1-a]isoquinolineYield 59.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-amino-5-chloroisoquinoline (6.1 g), ethyl 2-acetyl-2-bromoacetate (10.75 g) and sodium bicarbonate (14.36 g) in ethanol (72 ml) was refluxed for 2 hours and then filtered by suction. The filtrate was evaporated in vacuo, and the residue was dissolved in a mixture of chloroform and methanol. The solution was treated with silica gel (10 g) and filtered by suction. The filtrate was evaporated in vacuo and the residue was recrystallized from ethanol to give 7-chloro-3-ethoxycarbonyl-2-methylimidazo[2,1-a]isoquinoline (5.83 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationfiltered by suction
  3. customThe filtrate was evaporated in vacuo
  4. dissolutionthe residue was dissolved in a mixture of chloroform and methanol
  5. additionThe solution was treated with silica gel (10 g)
  6. filtrationfiltered by suction
  7. customThe filtrate was evaporated in vacuo
  8. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-f09bb7b220634684b31d4ae92978e497
Source dataset
uspto-grants-1988_04
Patent number
US04738967

Reaction notes

Loading…