Sodium hydride → 5-hydroxy-2-methyl-8-nitro-3,4-dihydro-2H-isoquinolin-1-one

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 5-fluoro-2-methyl-8-nitro-3,4-dihydro-2H-isoquinolin-1-one (2.24 g, 10 mmol) in DMF (15 mL) is added 2-(methylsulfonyl)ethanol (1.86 g, 15 mmol) and the solution cooled to 0° C. Sodium hydride (1.2 g, 30 mmol) is added and the reaction mixture allowed to warm to room temperature and then stirred for 1 hour. The mixture is quenched with a 1N HCl solution and partitioned between ethyl acetate and brine. The organic layer is concentrated to dryness and the crude organics purified by flash column chromatography to give 5-hydroxy-2-methyl-8-nitro-3,4-dihydro-2H-isoquinolin-1-one in 70% yields. 1H-NMR (400 MHz, δ, ppm) Acetone-d6: 2.85-3.0 (m, 2H), 3.06 (s, 3H), 3.6-3.7 (m, 2H), 7.05-7.1 (m, 1H), 7.35-7.41 (m, 1H), 9.62 (brs, 1H).

Provenance & Evidence