HCID 178418361, compound → HCID 178515179, compound

HRID 649598Notes

Reaction equation

HRID 649598 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:31](=[O:32])[C:11]3=[CH:12][NH:13][C:14]4[CH2:15][CH2:16][CH:17]([O:20]C(OCC5C=CC=CC=5)=O)[CH2:18][C:19]=4[C:10]3=[N:9]2)=[CH:4][CH:3]=1.[H][H]>CN(C=O)C.CCO.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:31](=[O:32])[C:11]3=[CH:12][NH:13][C:14]4[CH2:15][CH2:16][CH:17]([OH:20])[CH2:18][C:19]=4[C:10]3=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178525172HCID 178525172, compound

Product 1

HCID 178515179HCID 178515179, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

2-p-chlorophenyl-8-benzyloxycarbonyloxy-2,3,6,7,8,9-hexahydropyrazolo[4,3-c]quinolin-3(5H)-one (1.60 g) is dissolved in 100 mL of 1:1 mixture of DMF and EtOH and subjected to catalytic hydrogenation with 10% palladium on carbon (0.4 g) for 24 hours under one atmosphere pressure of hydrogen. After the reaction is complete the catalyst is filtered off and the filtrate is evaporated to dryness. The residue is triturated with EtOH to obtain 2-p-chlorophenyl-8-hydroxy-2,3,6,7,8,9-hexahydropyrazolo[4,3-c]quinolin-3(5H)-one.

Workup

  1. filtrationis filtered off
  2. customthe filtrate is evaporated to dryness
  3. customThe residue is triturated with EtOH

Sources & evidence

ORD record
ord-34bbdaed5a054a849f15b92b650d56ae
Source dataset
uspto-grants-1988_04
Patent number
US04740512

Reaction notes

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