Acetone → 8-((4-Isopropylamino-1-methylbutyl)amino)-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline Succinate

Participants

Reaction Steps

A solution of 8-(4-amino-1-methylbutylamino)-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline as the free base (4.7 g, 10.8 mmol) prepared as in Example 1 in EtOH (60 mL) containing acetone (1.8 mL), prereduced platinum oxide (0.6 g) and molecular sieves (3A) was reduced on a Parr apparatus at 45 psig for 5 hours. An additional quantity of acetone (0.9 mL) was added and the reduction was continued an additional 18 hours. The catalyst and molecular sieves were filtered (celite) and the solvent was removed in vacuo. The residue was dissolved in acetonitrile (50 mL) and succinic acid (1.35 g, 1 mol equivalent) was added with stirring. The solid was filtered after cooling in the refrigerator overnight to yield the title compound 5, 5.8 g (91%), mp 143°-146°. Recrystallization from acetonitrile (75 mL) yielded pure title compound, 5.2 g, (81%), mp 145°-147.5°.

Provenance & Evidence