Succinic Acid → Tafenoquine succinate

Participants

Reaction Steps

A mixture of the product from example 2.2 (7.5 g, 15.2 mmol), ethanol (150 ml) and 5% Pd—C (2 g) was stirred under ca. 1 bar hydrogen for 24 hours at ambient temperature. The catalyst was filtered off and the solvent evaporated to leave a volume of ca. 25 ml. Succinic acid (2.3 g, 19.8 mmol) was added, and the mixture heated under reflux for 30 minutes. The solution was then cooled to 0–5° C., seeded with authentic target compound, and stirred for 2 hours. The crystalline product was filtered off, washed with ethanol (15 ml) and dried in vacuo at 50° C. for 24 hours to give 8-[(4-amino-1-methylbutyl)amino]-2,6-dimethoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline succinate as an off-white crystalline solid (6.0 g, 68%).

Provenance & Evidence