6-Quinolinecarboxylic acid → 1,2,3,4-Tetrahydroquinoline-6-carboxylic acid

HRID 1770096Notes

Reaction equation

HRID 1770096 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 825716-Quinolinecarboxylic acidHCID 2723923Ammonium formate

Product 1

HCID 27796411,2,3,4-Tetrahydroquinoline-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Quinoline-6-carboxylic acid (1.0 eq, 14.01 mmol) and ammonium formate (22 g, 350.1 mmol) were dissolved in MeOH (100 mL) and 10% Pd/C (4.04 g) was added. The solution was heated at reflux for 2.5 h then cooled to room temperature and filtered through celite. The solvent was removed to provide 1,2,3,4-tetrahydroquinoline-6-carboxylic acid in quantitative yield. 1H NMR (200 MHz, DMSO) δ1.78 (m, 2H), 2.65 ((m, 2H), 3.2 (m, 2H), 6.4 (m, 2H), 7.45 (m, 2H).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 2.5 h
  3. filtrationfiltered through celite
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-217871c24d964720afadc059cd957f58
Source dataset
uspto-grants-1995_01
Patent number
US05385909

Reaction notes

Loading…