Hydroxylamine → Methyl 4-[amino(hydroxyimino)methyl]-3-fluorobenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-cyano-3-fluorobenzoate obtained in Step 1 (834.5 mg; 4.66 mmol) in EtOH (9 mL) was added hydroxylamine (50% in water, 1.37 mL; 23.29 mmol). The solution was stirred at 74° C. for 4 h. The solvents were evaporated and the residue was taken in EtOAc (20 mL), washed with brine (3×15 mL), dried over MgSO4 and evaporated, affording the title compound as a yellow solid. 1H NMR: (DMSO-d6, 300 MHz) δ 9.89 (s, 1H), 7.92 (t, J=7.91 Hz, 1H), 7.69 (dd, J=1.70 Hz, J=8.10 Hz, 1H), 7.64 (dd, J=1.51 Hz, J=12.81 Hz, 1H), 5.97 (s, 2H), 3.92 (s, 3H). HPLC (Method A) Rt 2.90 min (Purity: 90.3%).

Provenance & Evidence