Water → 7-Hydroxy-3-quinolinecarbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-3-formylquinolin-7-yl acetate (2.9 g, 14 mmol) and Pd(PPh3)4 (1.6 g, 1.4 mmol, 0.1 eq.), Et3N (17 g, 168 mmol, 16 eq.) in DMF (100 mL) was added formic to acid (3.48 g, 75.6 mmol, 5.4 eq.) dropwise over 5 min. The mixture was warmed to 110° C. over 2 h. Then, the reaction mixture was diluted (water), extracted (EA), washed (brine), dried (Na2SO4), filtered and evaporated to dryness to give the crude product, which was purified by silica gel column chromatography (PE-EA, 1:1) to give desired compound as yellow solid (1.45 g, yield 60%). ESI-MS: 216 (M+H)+. 1H NMR (300 MHz, CDCl3) δ: 7.26-7.32 (m, 2H), 8.04-8.07 (d, 1H), 8.78 (d, 1H), 9.13 (s, 1H), 10.13 (s, 1H).

Provenance & Evidence