HCID 178418361, compound → HCID 178515179, compound

HRID 1905703Notes

Reaction equation

HRID 1905703 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-0fb4957907f64723beede2f30d75d945
Source dataset
uspto-grants-1987_03
Patent number
US04647566

Reaction notes

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