Ammonia → HCID 11813010, compound

Participants

Reaction Steps

A suspension of 2,6-bis(3-pyrrolidinopropionamido)acridone AR-ACO-10 (2.0 g, 4.2 mmol) in CHCl3 (40 mL) was treated with phosphorus pentachloride (0.9 g, 4.2 mmol), followed by cautious addition of phosphorus oxychloride (50 mL). This suspension was stirred at room temp. for 30 min and brought to a gentle reflux over 1 hr. Gentle reflux was maintained for 26 hr. The reaction mixture was cooled to rt then slowly dropped onto ice (˜600 mL) over 10 min. The aqueous mixture was made basic to pH 7/8 with ammonia whilst maintaining a temp. <25° C. The aqueous layer was extracted with CHCl3 (5×200 mL). The organic extracts were combined, washed with brine (200 mL), dried (Na2SO4) and concentrated. The resulting solid was tritrated with diethyl ether (30 mL) to give the desired product (1.3 g, 62%) as a light brown solid.

Provenance & Evidence