Formic Acid → Bmy 25368

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-amino-2-[3-(3-formylphenoxy)propylamino]-1-cyclobutene-3,4-dione (6.0 g, 21.8 mmole) in 150 mL of toluene was treated with piperidine (4.3 mL, 3.7 g, 43.6 mmole) and the mixture was heated to 65° C., and then cooled to about 30° C. Formic acid (2.2 mL of 95% aqueous formic acid containing 2.5 g formic acid, 55.4 mmole) was added. The mixture was heated to reflux temperature and the water formed was collected by azeotropic distillation. When the distillate became clear and gas evolution had ceased (about 30 minutes at reflux), the mixture was cooled and the solids were collected by filtration, washed with toluene, methanol and dried to yield 4.7 g (62.8%) of the title compound; mp=223°-228° C.

Provenance & Evidence