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

HRID 1385044Notes

Reaction equation

HRID 1385044 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]>C(O)C.[Pd]>[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 l of ethanol and admixed with 10.0 g of palladium on activated carbon (5%). Over a period of 48 hours, the mixture was reduced in an autoclave at 50° C. using hydrogen (1 bar) (HPLC control). The reaction mixture was then filtered, the filter cake was washed with ethanol and the combined organic filtrates were concentrated.

Workup

  1. customwas reduced in an autoclave at 50° C.
  2. filtrationThe reaction mixture was then filtered
  3. washthe filter cake was washed with ethanol
  4. concentrationthe combined organic filtrates were concentrated

Sources & evidence

ORD record
ord-d95a369dc23b41f4a78cbb3cc939dca0
Source dataset
uspto-grants-2001_07
Patent number
US06262074B1

Reaction notes

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