Chloroform → 9-Methoxy-5-methyl-2-(2-methylphenyl)imidazo[2,1-a]isoquinoline

HRID 376320Notes

Reaction equation

HRID 376320 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([CH3:23])[N:9]3[CH:15]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[CH3:22])[N:13]=[C:10]32)=[CH:5][CH:4]=1.C(Cl)(Cl)Cl>C1C2C(CCCC2)CCC1.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([CH3:23])[N:9]3[CH:15]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[CH3:22])[N:13]=[C:10]32)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 6212ChloroformHCID 18691224HCID 18691224, compound

Product 1

HCID 186912069-Methoxy-5-methyl-2-(2-methylphenyl)imidazo[2,1-a]isoquinolineYield 61.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7044DecalinSolvent

Procedure

To a solution of 4.9 g of 9-methoxy-5-methyl-2-(2-methylphenyl)-5,6-dihydroimidazo[2,1-a]isoquinoline in 30 ml of decalin was added 0.97 g of palladium on activated carbon (Pd 10%) and the mixture was refluxed for 6 hours. After being cooled and an addition of 200 ml of chloroform, the mixture was filtered and the filtrate was evaporated in vacuo. The resultant residue was crystallized from a mixture of hexane and ethyl acetate(6:1) to give 3.0 g of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. temperatureAfter being cooled
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated in vacuo
  5. customThe resultant residue was crystallized from a mixture of hexane and ethyl acetate(6:1)

Sources & evidence

ORD record
ord-642cb24e823a4997b41d9ec7ebc93a14
Source dataset
uspto-grants-2000_02
Patent number
US06020342

Reaction notes

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