Isoquinoline → 5-Nitroisoquinoline

Participants

Reaction Steps

To a solution of isoquinoline (120 g, 0.929 mol) in H2SO4 (1 L) was added KNO3 (112.6 g, 1.115 mol) at −15° C. (dropwise). The mixture was stirred at room temperature for 2 hours. TLC (petroleum ether:ethyl acetate=2:1) showed complete conversion. The mixture was added to water (3 L) at 0° C. The mixture was adjusted to pH 8 by the addition of NH4OH and filtered. The filter cake was washed with methyl tertbutyl ether (1 L×2) and concentrated under vacuum to give 5-nitro-isoquinoline (160 g, 94%) as a yellow solid.

Provenance & Evidence