Sodium Hydroxide → HCID 59490683, compound

Participants

Reaction Steps

To a solution of ethyl 3-(6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamido)benzoate (0.593 g, 1.62 mmol) in methanol (10 mL) was added aqueous NaOH (0.64 g in 6 mL of H2O, 16.2 mmol). The reaction was stirred at room temperature for 16 hours. The solvent was then removed under reduced pressure the resulting aqueous solution acidified to pH<2 using 2N HCl. A white precipitate crashed out, which was filtered, washed with water and dried to give the pure desired product, 3-(6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamido)benzoic acid (0.539 g, 98%) as a white solid; M.p.=237-241° C.; 400 MHz 1H NMR (DMSO-d6) δ: 9.0 (s, 1H), 8.41 (s, 1H), 8.26 (s, 1H), 8.14-8.1 (m, 1H), 7.82-7.78 (m, 1H), 7.56-7.51 (m, 1H), 7.4-7.34 (m, 1H), 4.81 (s, 2H), 3.86 (t, J=6 hz, 2H), 3.18 (t, J=6 Hz, 2H); LCMS [M+H]: 338.

Provenance & Evidence