Phosphorus oxychloride → Methyl 2-chloroquinoline-4-carboxylate

Participants

Reaction Steps

A stirred solution of 4-carbomethoxy quinolin-2-one (prepared as shown in Method D (1.76 g, 9 mmol), POCl3 (4.6 g, 30 mmol) in toluene (40 mL) was heated at reflux for 2 h then allowed to cool to room temperature and poured into ice water (50 mL). The mixture was extracted with ethyl acetate (3×50 mL). The organics were combined, washed with water, brine, dried (MgSO4) and concentrated in vacuo to afford the desired 2-chloro-4-carbomethoxyquinoline lv (1.50 mg). 1H NMR (DMSO-d6) δ 8.54 (d, J=8 Hz, 1H), 8.03-8.06 (m, 1H), 7.89-7.94 (m, 2H), 7.75-7.77 (m, 1H), 3.98 (s, 3H); ESI-MS m/z 222.1 (100, M+H+).

Provenance & Evidence