Formic Acid → HCID 18439913, compound

Participants

Reaction Conditions

Reaction Steps

Formic anhydride was prepared by placing 260 mg (5.66 mmoles) of formic acid into a dry 100 mL round-bottom flask equipped with a condenser, magnetic stirrer and a nitrogen inlet. The flask was cooled with an ice bath and then 470 mg (4.61 mmoles) of acetic anhydride was added. The stirring solution was then gently warmed to 50° C. with an oil bath for 2 hrs. After this time the reaction was cooled, and 25 mL of dry THF was added followed by the addition of 1.0 g (3.77 mmoles) of 2-(3-methoxyphenyl)-4,6-quinolinediamine as a solution in 10 mL of dry THF. The mixture was then heated to reflux for 2 hrs. At the end of this time the reaction was cooled and ether was added. The solids which formed were then collected by filtration and washed with ether. The solids were then dissolved in ethyl acetate and 5% NaOH solution, the layers separated and the organic layer dried over Na2SO4, filtered and concentrated to give 830 mg (75%) of the desired product. This product was used without further purification.

Provenance & Evidence