Acetic Anhydride → HCID 19592733, compound

HRID 613561Notes

Reaction equation

HRID 613561 reaction equation
[NH2:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]3[C:10]([NH:15][C:16](=[O:25])[C:17]4[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=4[Cl:24])=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]=2[NH:4][N:3]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>ClCCCl>[C:26]([N:3]1[C:2](=[NH:1])[C:6]2[CH:7]=[N:8][C:9]3[C:10]([NH:15][C:16](=[O:25])[C:17]4[C:18]([Cl:24])=[CH:19][CH:20]=[CH:21][C:22]=4[Cl:23])=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]=2[NH:4]1)(=[O:28])[CH3:27].[C:26]([NH:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]3[C:10]([NH:15][C:16](=[O:25])[C:17]4[C:18]([Cl:24])=[CH:19][CH:20]=[CH:21][C:22]=4[Cl:23])=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]=2[NH:4][N:3]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 19592706HCID 19592706, compound

Product 2

HCID 19592733HCID 19592733, compoundHCID 178474000HCID 178474000, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of 3-amino-6-(2,6-dichlorobenzoylamino)-1H-pyrazolo[4,3-c]quinoline (200 mg) in 1,2-dichloroethane (2 ml) was added acetic anhydride (302 mg), and the reaction mixture was refluxed for 12 hours. The solution was allowed to cool to ambient temperature and the solvent was evaporated in vacuo. The residue was triturated with water-ethanol, and the precipitate was collected. The crude product was purified by column chromatography on silica gel (ethyl acetate-n-hexane) to give 2-acetyl-6-(2,6-dichlorobenzoylamino)-2,3-dihydro-3-imino-1H-pyrazolo[4,3-c]-quinoline as a yellow crystal (60 mg) and 3-acetamido-6-(2,6-dichlorobenzoylamino)-1H-pyrazolo[4,3-c]quinoline as a white crystal (30 mg). 2-Acetyl-6-(2,6-dichlorobenzoylamino)-2,3-dihydro-3-imino-1H-pyrazolo[4,3-cilquinoline

Workup

  1. temperaturethe reaction mixture was refluxed for 12 hours
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was triturated with water-ethanol
  4. customthe precipitate was collected
  5. customThe crude product was purified by column chromatography on silica gel (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-fc2558baac1e4a9fb35b0f1bdd1d8b0f
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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