Hydrochloric Acid → Ethyl 3-oxo-3-(quinolin-2-yl)propanoate

HRID 52542Notes

Reaction equation

HRID 52542 reaction equation
[N:1]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:2]=1[CH2:3][C:4](OCC)=O.[C:17]([O:20][CH2:21][CH3:22])(=[O:19])C.[O-:23]CC.[Na+].Cl>C1(C)C=CC=CC=1>[CH2:21]([O:20][C:17]([CH2:4][C:3]([C:2]1[CH:9]=[CH:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:1]=1)=[O:23])=[O:19])[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 2723922Sodium ethoxideHCID 12481727Ethyl (quinolin-2-yl)acetate

Product 1

HCID 13550005Ethyl 3-oxo-3-(quinolin-2-yl)propanoateYield 46.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl quinaldinate (58.0 g, 0.288 mol), ethyl acetate (42.6 mL, 0.432 mol), and sodium ethoxide (29.4 g, 0.432 mol) in toluene (1 L) was heated at reflux temperature for 2 h. The mixture was neutralized by addition of diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, and concentrated. The residue was purified with silica gel column chromatography with 15:1 to 3:1 hexane/ethyl acetate to give 32.34 g of 2-ethoxycarbonylmethylcarbonylquinoline (46%): 1H NMR (270 MHz, CDCl3) δ8.28 (d, 1H, J=8.3 Hz), 8.17 (dd, 1H, J=8.2, 1 Hz), 8.14 (d, 1H, J=8.3 Hz), 7.84 (dd, 1H, J=8.2, 1 Hz), 7.79 (td, 1H, J=8.2, 1 Hz), 7.66 (td, 1H, J=8.2, 1 Hz), 4.36 (s, 2H), 4.22 (q, 2H, J=7.3 Hz), 1.24 (t, 3H, J=7.3 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 2 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified with silica gel column chromatography with 15:1 to 3:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-55d8141ef56a4334b486705419139546
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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