HCID 10857784, compound → HCID 23359069, compound

HRID 232710Notes

Reaction equation

HRID 232710 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH:9]=[CH:8]2>[Pd].C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9][CH2:8]2

Participants

4

Reactant 1

HCID 10857784HCID 10857784, compound

Product 1

HCID 23359069HCID 23359069, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

0.12 g of 10% Pd-C was added to 20 ml of an acetic acid solution containing 1.20 g of 8-methoxy-6-ethoxycarbonylcarbostyril. The mixture was subjected to hydrogenation at 90° C. at normal pressure for 1 hour. The catalyst in the reaction mixture was removed by filtration. The filtrate was subjected to distillation to remove the solvent. The residue was purified by a silica gel column chromatography (elutant: chloroform) and recrystallized from chloroform-diethyl ether to obtain 0.85 g of 8-methoxy-6-ethoxycarbonyl-3,4-dihydrocarbostyril as a white powder.

Workup

  1. customThe catalyst in the reaction mixture was removed by filtration
  2. distillationThe filtrate was subjected to distillation
  3. customto remove the solvent
  4. customThe residue was purified by a silica gel column chromatography (elutant: chloroform)
  5. customrecrystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-ce896f78f427464fbb50779942d6a024
Source dataset
uspto-grants-1997_01
Patent number
US05591751

Reaction notes

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