Methylamine → 2-Methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one

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Reaction Steps

At room temperature, a solution of methyl 2-bromomethyl-6-nitrobenzoate (1.26 g, 4.63 mmol) in THF (13 mL) is treated with 2M soln. of methylamine in THF (14 mL), stirred for 5 h, diluted with EtOAc (100 mL), washed with sat. aqueous solution of NaHCO3 (15 mL) and brine (15 mL), dried (MgSO4), and evaporated. A flash chromatography (30 g of silica gel; CH2Cl2/EtOAc 1:1) gives N-Methyl-7-nitro-2,3-dihydroisoindole-1-one (0.561 g, 2.92 mmol) in 63%. Yellow solid. Rf (CH2Cl2/EtOAC 1:1) 0.46. 1H-NMR (400 MHz, CDCl3) 3.21 (s), 4.44 (s), 7.63-7.69 (m, 2H), 7.70-7.75 (m, 1H).

Provenance & Evidence