HCID 19603497, compound → HCID 19603455, compound

HRID 1604581Notes

Reaction equation

HRID 1604581 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])C1C=CC=CC=1>C(O)C.O1CCOCC1.[OH-].[Pd+2].[OH-]>[CH2:23]([O:22][C:20]([C:14]1[C:13]2[C:18](=[C:9]([OH:8])[CH:10]=[CH:11][CH:12]=2)[N:17]=[C:16]([CH3:19])[CH:15]=1)=[O:21])[CH3:24]

Participants

5

Reactant 1

HCID 19603497HCID 19603497, compound

Product 1

HCID 19603455HCID 19603455, compoundYield 77.6%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8-benzyloxy-4-ethoxycarbonyl-2-methylquinoline (663 mg) and palladium(II) hydroxide (60 mg) in a mixture of ethanol (6 ml) and dioxane (6 ml) was stirred for 3 hours at ambient temperature under hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated. The residue was pulverized with n-hexane to give 4-ethoxycarbonyl-8-hydroxy-2-methylquinoline (370 mg) as pale yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ab303aaac5764b7e97be16f7345babf4
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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