Sodium Carbonate → HCID 13019470, compound

Participants

Reaction Steps

A solution of sodium nitrite (0.5 g) in water (5 ml) was added dropwise to a stirred solution of 4-[3-(N,N-dimethylamino)-1-(imidazol-2-yl)propyl]benzoic acid hydrazide (2.0 g) in 2 N hydrochloric acid (10.5 ml) and water (50 ml) at 0° to 5° C. After 30 min. the solution was basified by adding 2 N sodium carbonate (15 ml) and then extracted with ether (3×50 ml). The extracts were dried (Na2SO4) and concentrated to an off white solid (1.7 g). This solid was dissolved in toluene (40 ml) and benzyl alcohol (1.5 ml) and heated on a steam bath for 2 h. Solvent was removed and the residue taken up in ethanol (20 ml) and hydrogenated at atmospheric pressure over 10% palladium oxide on charcoal (0.5 g) for 3 h. The catalyst was filtered off and the filtrate treated with a solution of maleic acid (1.8 g) in ethanol (10 ml). Removal of the solvent and trituration of the residue with dry ether afforded a white solid. Recrystallisation from ethanolether gave the trimaleate salt of the title compound, m.p. 132°-133° (2.6 g).

Provenance & Evidence