Hydrochloric Acid → HCID 178432236, compound

Participants

Reaction Conditions

Reaction Steps

Under an N2 atmosphere, 4-fluorobenzene-1,2-diamine (5.00 g, 39.6 mmol) was suspended in EtOH (220 mL) and 5M HCl (160 mL) was added. The reaction was warmed to 50° C. and 2,4-pentandione (8.14 mL, 7.93 mmol) was added and the reaction was heated to reflux for 30 min. Upon cooling to room temperature, the reaction was neutralized with a saturated solution of NaHCO3(aq) and extracted with dichloromethane. The layers were separated and the aqueous layer was washed with additional dichloromethane (2×). The organics were then combined, dried (Na2SO4), filtered and concentrated in vacuo. The resulting solid was triturated with dichloromethane to afford the title compound. 1H NMR (400 MHz) (DMSO-d6) δ 7.43-7.19 (bm, 2H); 6.92 (bs, 1H); 2.44 (s, 3H).

Provenance & Evidence