ethyl quinoline-3-carboxylate → Ethyl 1,2,3,4-tetrahydroquinoline-3-carboxylate

HRID 1803768Notes

Reaction equation

HRID 1803768 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]([O:13][CH2:14][CH3:15])=[O:12])[CH:2]=1>[Pd].C(O)C>[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:2]1

Participants

4

Reactant 1

HCID 282842ethyl quinoline-3-carboxylate

Product 1

HCID 12415759Ethyl 1,2,3,4-tetrahydroquinoline-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl quinoline-3-carboxylate (Aldrich, 15.44 g, 76.7 mmol) was added to a mixture of ethanol (150 mL) and 10% palladium on carbon (3.0 g) in a Parr shaker. The glass reactor was sealed and flushed with nitrogen, and pressurized with hydrogen (60 psi). The mixture was shaken at 50° C. for 52 hours. The solids were filtered, rinsed with methanol, concentrate under reduced pressure, and chromatographed on silica gel eluting with 5-40% ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.19 (t, J=7.12 Hz, 3H), 2.83 (m, 3H), 3.17 (m, 1H), 3.39 (m, 1H), 4.09 (q, J=7.12 Hz, 2H), 5.74 (s, 1H), 6.44 (m, 2H), 6.86 (m, 2H). MS (DCI) m/z 206.10 (M+H)+.

Workup

  1. customThe glass reactor was sealed
  2. customflushed with nitrogen
  3. filtrationThe solids were filtered
  4. washrinsed with methanol
  5. concentrationconcentrate under reduced pressure
  6. customchromatographed on silica gel eluting with 5-40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5c33bd972187461f81c8c9030d8f511b
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

Loading…