Ethanol → ethyl quinoline-2-carboxylate

HRID 1803770Notes

Reaction equation

HRID 1803770 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=[O:12].S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([O:13][CH2:19][CH3:20])=[O:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 7124Quinaldic Acid

Product 1

HCID 421739ethyl quinoline-2-carboxylate

Procedure

Quinoline-2-carboxylic acid (Aldrich, 10.0 g, 57.7 mmol) was added to ethanol (500 mL) and sulfuric acid (25 mL) and refluxed for 7 hours. The mixture was concentrated under reduced pressure and dichloromethane (400 mL) was added. The organic layer was washed twice with saturated sodium bicarbonate (400 mL), dried with sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.39 (t, J=7.12 Hz, 3H), 4.43 (q, J=7.12 Hz, 2H), 7.76 (ddd, J=8.14, 6.95, 1.19 Hz, 1H), 7.88 (ddd, J=8.48, 6.95, 1.53 Hz, 1H), 8.11 (m, 2H), 8.18 (d, J=8.48 Hz, 1H), 8.58 (d, J=8.48 Hz, 1H). MS (DCI) m/z 202.05 (M+H)1.

Workup

  1. temperaturerefluxed for 7 hours
  2. concentrationThe mixture was concentrated under reduced pressure and dichloromethane (400 mL)
  3. additionwas added
  4. washThe organic layer was washed twice with saturated sodium bicarbonate (400 mL)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ccb15996bca34e0dad3395686ae02d81
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

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