Quinoline-3-carboxylic acid → 5,6,7,8-Tetrahydroquinoline-3-carboxylic acid

HRID 324518

Reaction equation

HRID 324518 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([OH:13])=[O:12])[CH:2]=1>FC(F)(F)C(O)=O.[Pt](=O)=O>[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([C:11]([OH:13])=[O:12])[CH:2]=1

Participants

4

Reactant 1

HCID 80971Quinoline-3-carboxylic acid

Product 1

HCID 217959145,6,7,8-Tetrahydroquinoline-3-carboxylic acidYield 43.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 3-quinolinecarboxylic acid (1.73 g, 10.0 mmol) in trifluoroacetic acid (20 ml) with platinum dioxide (200 mg) was shaken in a Parr vessel at 10-15 psi. After 90 minutes the reaction mixture was filtered and the solvent removed in vacuo to yield an oil. The oil was added dropwise onto diethyl ether yielding a white solid which was collected by filtration and then recrystallised from ethyl acetate/hexane to yield the title compound as a white solid (770 mg).

Workup

  1. filtrationAfter 90 minutes the reaction mixture was filtered
  2. customthe solvent removed in vacuo
  3. customto yield an oil
  4. additionThe oil was added dropwise onto diethyl ether yielding a white solid which
  5. filtrationwas collected by filtration
  6. customrecrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-292f9472f52d442095ef52e79c8a4349
Source dataset
uspto-grants-2001_04
Patent number
US06218393B1

Linked notes

Loading…