Hydrochloric Acid → HCID 59316601, compound

Participants

Reaction Steps

To the crude (tert-butyl 2-(6-(4-chlorophenyl)-7-methoxy-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate) form Example 4D was added 4N hydrochloric acid in 1,4-dioxane (10 mL, 40 mmol). The reaction mixture was stirred at room temperature for 4 hours, and concentrated under reduced pressure. A second portion of 4N hydrochloric acid in 1,4-dioxane (10 mL, 40 mmol) and anhydrous N,N-dimethylformamide (2 mL) were added, and the mixture stirred for another 13 hours. The solvent was removed under reduced pressure, and the crude reaction product subjected to reverse phase HPLC with a gradient of acetonitrile/water (2% to 98%) to afford 2-(6-(4-chlorophenyl)-7-methoxy-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetic acid (95 mg, 0.27 mmol, 72%). LCMS mz 346.0 (M+H), 368.0 (M+Na), anal HPLC >98% in purity. 1H NMR (400 MHz; CDCl3) δ 7.42 (d, J=8.6 Hz, 2H); 7.36 (d, J=8.6 Hz, 2H); 7.11 (s, 1H); 6.48 (s, 1H); 4.75 (s, 2H); 3.79 (s, 3H); 2.93 (m, 2H); 2.75 (m, 2H).

Provenance & Evidence