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 35684Notes

Reaction equation

HRID 35684 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 rated 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 residual solid was recrystallized from a mixture of methanol and chloroform

Sources & evidence

ORD record
ord-d3034ecf9f19426b80d3d147b4173e6a
Source dataset
uspto-grants-1988_08
Patent number
US04767780

Reaction notes

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