Methyl iodide → Methyl 5-bromoquinoline-8-carboxylate

Reaction equation

[Br:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([OH:14])=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:15](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

Procedure

To a solution of 5-Bromoquinoline-8-carboxylic acid (30 g, 0.119 mol, crude) in DMF (400 ml) was added potassium carbonate (41.12 g, 0.297 mol) and MeI (22.3 ml, 0.357 mol) at RT. The reaction mixture was stirred at RT for 12 h and the reaction completion was confirmed by TLC. After completion of reaction the reaction mixture was filtered and evaporated. The reaction mixture was basified with 10% NaHCO3 and extracted with ethyl acetate. The organic layer was washed with water, brine and dried over sodium sulphate and concentrated to afford the title compound as brown liquid (4.6 g). LCMS: Mass found (M+, 268). 1H NMR (DMSO-d6 400 MHz): δ 9.04-9.02 (dd, J=3.92, 5.68, Hz, 1H), 8.58-8.56 (m, 1H), 8.05-8.03 (d, J=7.72 Hz, 1H), 7.87-7.86 (d, J=7.76 Hz, 1H), 7.78-7.75 (dd, J=8.6, 12.8 Hz, 1H), 3.91 (s, 3H).