HCID 19363338, compound → HCID 19363376, compound

HRID 850432Notes

Reaction equation

HRID 850432 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH:20][C:21]([OH:23])=[O:22].[H][H]>[C].[Pd].CO>[CH3:13][O:12][C:8]1[C:7]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:6]2[C:11]([CH:2]=[C:3]([NH:20][C:21]([OH:23])=[O:22])[CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 19363338HCID 19363338, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19363376HCID 19363376, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

4-Chloro-7-methoxy-8-pentyloxyquinoline-3-carbamic acid (101 mg, 0.312 mmol) and methanol (10 ml) were mixed, and 10% palladium-carbon catalyst (30 mg) was added to this solution. The mixture was stirred at room temperature for 5 hours in a stream of hydrogen. The palladium-carbon catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (hexane/ethyl acetate=10/1-6/4) to give 7-methoxy-8-pentyloxyquinoline-3-carbamic acid (74.6 mg, 83%) as yellow crystals.

Workup

  1. filtrationThe palladium-carbon catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by column chromatography (hexane/ethyl acetate=10/1-6/4)

Sources & evidence

ORD record
ord-7d5eb232fd91450e8e44493f91711d0a
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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