Hydrochloric Acid → HCID 70874054, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-bromo-5-chloro-3-[ethyl(oxan-4-yl)amino]benzoate (122 mg, 0.32 mmol) in tetrahydrofuran (3 ml) was added 4M NaOH (3.2 ml). The reaction mixture was stirred at 50° C. for 20 hours. The reaction mixture was acidified to pH 2-3 with 6M HCl and extracted with DCM (3×100 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give 109 mg (93%, 83% corrected yields) of 2-bromo-5-chloro-3-[ethyl(oxan-4-yl)amino]benzoic acid as a pale yellow foam. LC-MS 89%, m/z=361.9/364.2/365.8, 1H NMR (500 MHz, Chloroform-d) δ 7.50 (d, J=2.4 Hz, 1H), 7.23 (d, J=2.4 Hz, 1H), 4.00 (d, J=11.5 Hz, 2H), 3.49-3.27 (m, 2H), 3.21 (t, J=7.4 Hz, 1H), 3.14 (q, J=7.0 Hz, 2H), 1.78 (dd, J=7.4, 3.4 Hz, 4H), 0.93 (t, J=7.0 Hz, 3H).

Provenance & Evidence