Hazard and Precautionary Statements (GHS)

Bucromarone Chemical Properties,Usage,Production

Originator

Bucromarone,Transphyto

Uses

Cardiac depressant (anti-arrhythmic).

Uses

Bucromarone is an antiarrhythmic drug.

Definition

ChEBI: Bucromarone is an aromatic ketone.

Manufacturing Process

1.2 mol of an electrophilic catalyst, advantageously aluminum chloride, was slowly added to a solution of 48.8 g (0.4 mol) of 2,6-dimethyl phenol in 400 ml of dichloroethane and agitated at room temperature for an hour. The mixture was cooled to 0°C and a solution of 84.0 g (0.4 mol) of 2-carboxylic chromone acid chloride in 400 ml of a dichloroethane, was slowly added. Agitation was continued at 0°C for 5 h and then at room temperature for 4 days. The reaction mixture was poured into 1.6 L of iced 50% hydrochloric acid. The resulting precipitate was filtered, washed with water, dried and 106.0 g (72% yield) of 2-(3,5-dimethyl-4-hydroxybenzoyl)chromone, melting point 216°C (recrystallised from dioxane) were obtained.
6.9 g (0.05 mol) of potassium carbonate was added to a solution of 29.4 g (0.1 mol) of 2-(3,5-dimethyl-4-hydroxybenzoyl)chromone in 250 ml of dimethyl formamide and kept at 100°C for an hour. A solution of 20.5 g (0.1 mol) of 3-N,N-dibutylamino-1-chloropropane in 100 ml of diethyl formamide was then added and the resulting solution heated to 130°C for 3 h. The solution was filtered, the dimethyl formamide was concentrated, dissolved in 300 ml water and extracted twice with 200 ml of benzene. The organic phase was dried on magnesium sulfate and the hydrochloride was precipitated by adding hydrochloric ether. 40.0 g (yield 80%) of 2-[4-(3-N,N-dibutylaminopropoxy)- 3,5-dimethylbenzoyl]chromone were obtained (recrystallised from an acetone/ether mixture).

Therapeutic Function

Antiarrhythmic, Coronary vasodilator