4,5-dihydro-8-nitro-5-propionyl-1H-pyrazolo[4,3-c]quinoline → 8-amino-4,5-dihydro-5-propionyl-1H-pyrazolo-[4,3-c]quinoline

HRID 653134Notes

Reaction equation

HRID 653134 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:11]2[N:10]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:9][C:8]3[CH:18]=[N:19][NH:20][C:7]=3[C:6]=2[CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][C:11]2[N:10]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:9][C:8]3[CH:18]=[N:19][NH:20][C:7]=3[C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 137452084,5-dihydro-8-nitro-5-propionyl-1H-pyrazolo[4,3-c]quinoline

Product 1

HCID 137452288-amino-4,5-dihydro-5-propionyl-1H-pyrazolo-[4,3-c]quinolineYield 81.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4,5-dihydro-8-nitro-5-propionyl-1H-pyrazolo[4,3-c]quinoline (1.36 g) in methanol (250 ml) was hydrogenated over 5% palladium on carbon (0.4 g) under atmospheric pressure at ambient temperature. After the theoretical amount of hydrogen gas was absorbed, the catalyst was filtered off and the filtrate was evaporated in vacuo. The residual solid was recrystallized from a mixture of methanol and chloroform to give 8-amino-4,5-dihydro-5-propionyl-1H-pyrazolo-[4,3-c]quinoline (0.981 g).

Workup

  1. customAfter the theoretical amount of hydrogen gas was absorbed
  2. filtrationthe catalyst was filtered off
  3. customthe filtrate was evaporated in vacuo
  4. customThe residual solid was recrystallized from a mixture of methanol and chloroform

Sources & evidence

ORD record
ord-dedac8bab0514dc08a6140ef005cf88d
Source dataset
uspto-grants-1987_06
Patent number
US04675324

Reaction notes

Loading…