2,5-Dimethoxytetrahydrofuran → 6-(1H-Pyrrol-1-yl)isoquinoline-1,3(2H,4H)-dione

Participants

Reaction Steps

A mixture of 6-amino-4H-isoquinoline-1,3-dione (1 g, 5.68 mmol), 2,5-dimethoxytetrahydrofuran (0.736 mL, 5.68 mmol), 4-chloropyridine hydrochloride (0.417 g, 2.78 mmol) in dioxane (20 mL) is heated at 70° C. for 2 h [Ref: J. Heterocyclic Chem. 35, 1313, (1998)] After cooling, the solid is filtered, washed successively with water, ether and hexane to yield 0.86 g (67%) of the title compound as a light brown solid, mp 212-213° C.; HRMS (ESI) m/z calcd for C13H10N2O2 227.08151. found 227.08151 (M+H)+1. Analysis for C13H10N2O2 (0.5H2O): Calcd: C, 66.37; H, 4.71; N, 11.91. Found: C, 66.19; H, 4.56; N, 11.09.

Provenance & Evidence