HCID 135773201, compound → HCID 135773203, compound

HRID 904686Notes

Reaction equation

HRID 904686 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([O:20][CH3:21])=[O:19])[CH:8]=[C:7]2SCC)(=[O:3])[CH3:2]>[Ni]>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([O:20][CH3:21])=[O:19])[CH:8]=[CH:7]2)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 135773201HCID 135773201, compound

Product 1

HCID 135773203HCID 135773203, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Methyl 6-acetyl-4-ethylthio-7-hydroxy-8-propylquinoline-2-carboxylate (1.0 g), was added to Raney Nickel (16 g wet wt; previously washed with ethanol) in dry ethanol (100 mls), and reflux for 11/2 hours. The catalyst was filtered off, and the filtrate evaporated to dryness. The residue was triturated with 40°-60° petroleum ether and the yellow solid collected by filtration to give 0.6 g of the sub-title product. A recrystallisation from ethanol gave 0.2 g, mp 110°-111°.

Workup

  1. washpreviously washed with ethanol) in dry ethanol (100 mls)
  2. temperaturereflux for 11/2 hours
  3. filtrationThe catalyst was filtered off
  4. customthe filtrate evaporated to dryness
  5. customThe residue was triturated with 40°-60° petroleum ether
  6. filtrationthe yellow solid collected by filtration

Sources & evidence

ORD record
ord-fc8d26a399404f3784b9ec097faeec07
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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