HCID 178436964, compound → HCID 178436969, compound

HRID 1666682Notes

Reaction equation

HRID 1666682 reaction equation
[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([OH:13])[C:4]=1[C:14]([O:16]CC1C=CC=CC=1)=[O:15])[CH3:2]>CO.C1COCC1.[Pd]>[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([OH:13])[C:4]=1[C:14]([OH:16])=[O:15])[CH3:2]

Participants

5

Reactant 1

HCID 178436964HCID 178436964, compound

Product 1

HCID 178436969HCID 178436969, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Benzyl 4-ethyl-2-hydroxyquinoline-3-carboxylate (1.2 g) was suspended in methanol (12 mL) and THF (6 mL), followed by addition of 5% Pd—C (120 mg), and the mixture was stirred at 40° C. for 1 day. The catalyst was removed by filtration, and then the filtrate was concentrated under reduced pressure to obtain 4-ethyl-2-hydroxyquinoline-3-carboxylic acid (0.85 g). This compound was used in the subsequent step without purification.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7e22c78a0c0f40379531f0d0cf8c108d
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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