3-Chloro-2,4-pentanedione → 3-Acetyl-7-chloro-2-methylimidazo[2,1-a]isoquinoline

HRID 649167Notes

Reaction equation

HRID 649167 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.Cl[CH:14]([C:18](=O)[CH3:19])[C:15](=[O:17])[CH3:16]>C(Cl)(Cl)Cl>[C:15]([C:14]1[N:3]2[CH:4]=[CH:5][C:6]3[C:11]([C:2]2=[N:1][C:18]=1[CH3:19])=[CH:10][CH:9]=[CH:8][C:7]=3[Cl:12])(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 743283-Chloro-2,4-pentanedioneHCID 138218255-Chloroisoquinolin-1-amine

Product 1

HCID 201424373-Acetyl-7-chloro-2-methylimidazo[2,1-a]isoquinolineYield 9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 1-amino-5-chloroisoquinoline (10 g) in chloroform (150 ml) was added dropwise 3-chloro-2,4-pentanedione (11.3 g). The mixture was refluxed for 6 hours and then allowed to stand at room temperature over night. The mixture was washed successively with aqueous sodium bicarbonate and water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (200 g) with chloroform as an eluent to afford a solid. This solid was recrystallized from ethyl acetate to give 3-acetyl-7-chloro-2-methylimidazo[2,1-a]isoquinoline (1.3 g).

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. waitto stand at room temperature over night
  3. washThe mixture was washed successively with aqueous sodium bicarbonate and water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (200 g) with chloroform as an eluent
  7. customto afford a solid
  8. customThis solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-53ff80fa7c284be38898b66038a5c79b
Source dataset
uspto-grants-1988_04
Patent number
US04738967

Reaction notes

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