Water → 3-(4-Methylbenzylideneamino)-2-(2-methylphenyl)imidazo[2,1-a]isoquinoline

HRID 376327Notes

Reaction equation

HRID 376327 reaction equation
[NH2:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]3[C:14]([C:5]2=[N:4][C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])=[CH:13][CH:12]=[CH:11][CH:10]=3.[C:22]1([CH3:30])[CH:27]=[CH:26][C:25]([CH:28]=O)=[CH:24][CH:23]=1.O>CO>[CH3:30][C:22]1[CH:27]=[CH:26][C:25]([CH:28]=[N:1][C:2]2[N:6]3[CH:7]=[CH:8][C:9]4[C:14]([C:5]3=[N:4][C:3]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 77254-MethylbenzaldehydeHCID 15462240HCID 15462240, compound2×

Product 1

HCID 540654623-(4-Methylbenzylideneamino)-2-(2-methylphenyl)imidazo[2,1-a]isoquinolineYield 78.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5 g of 3-amino-2-(2-methylphenyl)imidazo[2,1-a]isoquinoline (Compound 3) in 50 ml of methanol was added 2.2 g of p-tolualdehyde. After the mixture was stirred at room temperature for 22 hours, it 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 recrystallization from ethyl acetate/petroleum ether gave 5.4 g of the title compound as yellow crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel, and recrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-096292280e864d28a40860e4d714fc69
Source dataset
uspto-grants-2000_02
Patent number
US06020342

Reaction notes

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