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

HRID 1788939Notes

Reaction equation

HRID 1788939 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-42b24e713fe94be38ed0e09db8750803
Source dataset
uspto-grants-1987_08
Patent number
US04686227

Reaction notes

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