Sodium Hydroxide → HCID 70873862, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl 3-[benzyl(ethyl)amino]-2-methylbenzoate (370 mg, 1.24 mmol) in THF (20 ml) and MeOH (5 ml) was added 2M NaOH (3.11 ml, 6.22 mmol) and the reaction was stirred at 50° C. for 16 h. The reaction was cooled to room temperature and the solvent removed in vacuo after which the aqueous solution was adjusted to pH1 using 1M HCl. The product was extracted into DCM (3×50 ml), washed with brine (20 ml), dried with Na2SO4 concentrated and filtered to afford the title compound as an orange oil (296 mg, 80%) which was used in the next stage without any further purification. LC-MS 91%, m/z=270.0, 1H NMR (500 MHz, Chloroform-d) δ 7.73 (d, J=7.5 Hz, 1H), 7.34-7.30 (m, 4H), 7.23 (dt, J=15.4, 6.9 Hz, 3H), 4.12 (d, J=13.5 Hz, 2H), 3.04-2.94 (m, 2H), 2.69 (s, 3H), 0.99 (t, J=7.0 Hz, 3H).

Provenance & Evidence