2-Ethoxalylmethylcarbonylquinoline → 1-(Quinolin-2-yl)ethan-1-one
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
Product 1
Reagents, catalysts & solvents 1
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).