4-Quinolinecarboxylic acid → Decahydro-4-quinolinecarboxylic acid

HRID 1709977Notes

Reaction equation

HRID 1709977 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=[O:12])=[CH:3][CH:2]=1>C(O)(=O)C.[Rh]>[NH:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH:4]([C:11]([OH:13])=[O:12])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 102434-Quinolinecarboxylic acid

Product 1

HCID 14835567Decahydro-4-quinolinecarboxylic acidYield 90%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 4-quinoline carboxylic acid (1.5 g., 8.6 mmoles) in acetic acid (30 ml) containing 5% Rh/Al2O3 (400 mg) was reduced (4.2 kg, 85° C.) in a steel bomb for 15 hours. After cooling, the catalyst was filtered and the solvent was evaporated to dryness. The residue was triturated with EtOH/Et2O (50/50), filtered and washed with a minimum of Et2O to give pure 4-decahydroquinoline carboxylic acid (1.4 g, 90%) as white crystals, mp >300° C., see Burckhardt, Helferick, L. Wissel, J. Prak. Chim. 39 (1966). An analytical sample of its hydrochloride salt was recrystalized in acetonitrile/water. (Found: C 54.19; H 8.62; N 6.33. Calc. for C10H18ClNO2 : C 54.66 H 8.26; N 6.38). 1H NMR 400 MHz (H2O) δ=1.3-1.5 (4H, m) 1.67-1.76 (1H,m) 1.82-2.04 (5H, m) 2.29-2.4 (1H, m) 2.62-2.7 (1H, d t) 3.01-3.17 (1H, m) 3.46-3.57 (2H,m) 7.89 (1H, broad s, exchangeable D2O) 8.29 (1H broad s, exchangeable D2O).

Workup

  1. custom(4.2 kg, 85° C.)
  2. customfor 15 hours
  3. temperatureAfter cooling
  4. filtrationthe catalyst was filtered
  5. customthe solvent was evaporated to dryness
  6. customThe residue was triturated with EtOH/Et2O (50/50)
  7. filtrationfiltered
  8. washwashed with a minimum of Et2O

Sources & evidence

ORD record
ord-433f3d7fac5d42cfa6358dcc4c720844
Source dataset
uspto-grants-1990_08
Patent number
US04952573

Reaction notes

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