Water → 2-(2-Methylphenyl)imidazo[2,1-a]isoquinoline

HRID 1871464Notes

Reaction equation

HRID 1871464 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](=O)[CH2:20]Br.C(=O)(O)[O-].[Na+].O>C(O)C>[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[N:1]=[C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][N:3]2[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 737421-IsoquinolinamineHCID 516892Sodium BicarbonateHCID 124306762-Bromo-2'-methylacetophenone

Product 1

HCID 186911442-(2-Methylphenyl)imidazo[2,1-a]isoquinolineYield 81.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.0 g of 1-aminoisoquinoline, 6.7 g of 2'-methyl-2-bromoacetophenone and 17.5 g of sodium bicarbonate in 50 ml of ethanol was refluxed for 2 hours. After being cooled, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel and recrystallized from dichloromethane/petroleum ether to give 4.4 g of the title compound as pale brown prisms.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter being cooled
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe drying agent was removed by filtration
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel
  9. customrecrystallized from dichloromethane/petroleum ether

Sources & evidence

ORD record
ord-fdfd97e202ae49fcbb8ac33cd0470003
Source dataset
uspto-grants-2000_08
Patent number
US06103736

Reaction notes

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