Acetic Acid → 1,4-Diketo-2,5-diethyl-3,6-bis(1-naphthyl)pyrrolo[3,4-c]pyrrole

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Reaction Conditions

Reaction Steps

In 36 mL of t-amyl alcohol, 7.3 g of potassium-t-butoxide were solved, and then 10 g of 1-naphthonitrile were added stirring the solution at 90° C. Into the solution, 6.7 mL of diisopropyl succinate were dropped taking time for 2 hours and were placed under reflux for one day. Next, 30 mL of methanol and 4.4 mL of acetic acid were added at 60° C. and then refluxed for 30 minutes. After cooling, the product was separated out through a filter and subsequently rinsed with methanol, thus resulting in a red powder. Next, 2.89 g of the resulting red powder were dissolved in 80 mL of DMF, and 2.1 g of potassium-t-butoxide were added and stirred for one hour. Then, 1.5 mL of methyl iodide was added and stirred at 65° C. for one day. After 50 mL of water was added, extraction was performed with dichloromethane. The extract was concentrated and refined through a column chromatography with silica gel and thus results in 1.5 g of yellow powder. The following is the results of 1H-NMR analysis.

Provenance & Evidence