Sodium Hydroxide → 1,3-Dimethyl-5-nitroisoquinoline

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Reaction Steps

1,3-Dimethylisoquinoline [(Chem. Lett., 1983, p. 791), 2.39 g, 15.20 mM], in concentrated sulfuric acid, (15 ml), was cooled to <4° C. A solution of potassium nitrate, (1.69 g, 16.72 mM), in concentrated sulfuric acid was added dropwise, maintaining the temperature below 4° C. After complete addition the solution was stirred at this temperature for a further 2 h then warmed to room temperature for 1 h. The reaction mixture was poured into ice water and the solution basified with sodium hydroxide and extracted with DCM. The extract was washed with brine, dried and concentrated to a yellow solid. Purification by silica gel chromatography afforded the title compound as a yellow crystalline solid.

Provenance & Evidence