2-Ethoxalylmethylcarbonylquinoline → 1-(Quinolin-2-yl)ethan-1-one

HRID 52543Notes

Reaction equation

HRID 52543 reaction equation
C([CH2:8][C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)=[O:10])(C(OCC)=O)=O>Cl>[C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)(=[O:10])[CH3:8]

Participants

3

Reactant 1

HCID 199632362-Ethoxalylmethylcarbonylquinoline

Product 1

HCID 3187031-(Quinolin-2-yl)ethan-1-oneYield 96.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-ethoxalylmethylcarbonylquinoline (32.24 g, 0.132 mol) in concentrated hydrochloric acid (300 mL) was refluxed for 4 h and concentrated in vacuo. The residue was dissolved in aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 20:1 to 7:1 hexane/ethyl acetate to give 21.72 g of 2-acetylquinoline (96%): 1H NMR (270 MHz, CDCl3) δ8.25 (d, 1H, J=8.6 Hz), 8.19 (dd, 1H, J=8.3, 1 Hz), 8.13 (d, 1H, J=8.6 Hz), 7.86 (dd, 1H, J=8.3, 1 Hz), 7.78 (td, 1H, J=8.3, 1 Hz), 7.64 (td, 1H, J=8.3, 1 Hz), 2.87 (s, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in aqueous sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography with 20:1 to 7:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-d2d9c123015b44638b752ce959daefa7
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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