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

HRID 1788940Notes

Reaction equation

HRID 1788940 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-ede232d689f540df962a4f077637f4cb
Source dataset
uspto-grants-1987_08
Patent number
US04686227

Reaction notes

Loading…