8-Methylquinoline-5-carboxylic acid → 8-Methyl-1,2,3,4-tetrahydroquinoline-5-carboxylic acid

HRID 1017130Notes

Reaction equation

HRID 1017130 reaction equation
[CH3:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.[H][H]>[Pd].C(O)C>[CH3:1][C:2]1[C:11]2[NH:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 129507838-Methylquinoline-5-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 139517338-Methyl-1,2,3,4-tetrahydroquinoline-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.1 mol of 8-methylquinoline-5-carboxylic acid was suspended in 1.5 1 of ethanol and admixed with 10.0 g of palladium on activated carbon (5%). In an autoclave, the mixture was reduced at 50° C. with hydrogen (1 bar) over a period of 48 hours (HPLC monitoring). The reaction mixture was subsequently filtered, the filter cake was washed with ethanol and the combined organic filtrates were concentrated.

Workup

  1. filtrationThe reaction mixture was subsequently filtered
  2. washthe filter cake was washed with ethanol
  3. concentrationthe combined organic filtrates were concentrated

Sources & evidence

ORD record
ord-ff2acbc3e664438e90c8f8519055686b
Source dataset
uspto-grants-2002_11
Patent number
US06479436B1

Reaction notes

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