3,4,5,6-Tetrahydrophthalic anhydride → 2,3,5,6,7,8-Hexahydrophthalazine-1,4-dione

Participants

Reaction Steps

3,4,5,6-Tetrahydrophthalic anhydride (25 g, 0.164 mol) was dissolved in 40% aqueous acetic acid (500 ml) with sodium acetate trihydrate (26.8 g, 0.197 mol) and hydrazine hydrate (9.58 ml, 0.197 mol). The reaction mixture was heated under reflux overnight and then allowed to cool. The resulting solid was collected by filtration, washed with water and diethyl ether and dried in vacio to give the title-product (23 g, 84%), 1H NMR (250 MHz, d6-DMSO) δ1.64 (4 H, br s, 2 of CH2), 2.34 (4 H, br s, 2 of CH2), 11.30 (2 H, br s, 2 of NH); MS (ES+) m/e 167 [MH]+.

Provenance & Evidence