Acetic Acid → 3-Amino-7-chloro-2-methylimidazo[2,1-a]isoquinoline

HRID 649156Notes

Reaction equation

HRID 649156 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]1[C:14]([N:15]=O)=[C:13]([CH3:17])[N:12]=[C:7]12.C(O)(=O)C>O.[Zn]>[NH2:15][C:14]1[N:6]2[CH:5]=[CH:4][C:3]3[C:8]([C:7]2=[N:12][C:13]=1[CH3:17])=[CH:9][CH:10]=[CH:11][C:2]=3[Cl:1]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 138218497-Chloro-2-methyl-3-nitrosoimidazo[2,1-a]isoquinoline

Product 1

HCID 201424413-Amino-7-chloro-2-methylimidazo[2,1-a]isoquinolineYield 80.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

Zinc powder (10.2 g) was added portionwise to a mixture of 7-chloro-2-methyl-3-nitrosoimidazo[2,1-a]isoquinoline (7.7 g) and acetic acid (100 ml) in water (77 ml) over a period of 7 hours and then the mixture was filtered by suction. The filtrate was evaporated in vacuo and the residue was extracted with chloroform after an addition of aqueous sodium bicarbonte to it. The extract was washed with water and evaporated in vacuo. The residual solid was washed with ethyl acetate and dried in a desiccator to give 3-amino-7-chloro-2-methylimidazo[2,1-a]isoquinoline (5.85 g).

Workup

  1. filtrationthe mixture was filtered by suction
  2. customThe filtrate was evaporated in vacuo
  3. extractionthe residue was extracted with chloroform
  4. additionafter an addition of aqueous sodium bicarbonte to it
  5. washThe extract was washed with water
  6. customevaporated in vacuo
  7. washThe residual solid was washed with ethyl acetate
  8. customdried in a desiccator

Sources & evidence

ORD record
ord-d6b7d2cda5e544c38c0a052e91cb32fd
Source dataset
uspto-grants-1988_04
Patent number
US04738967

Reaction notes

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