N,O-Dimethylhydroxylamine → 5-bromo-N-methyl-N-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxamide

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Reaction Steps

A mixture of 5-bromo-3,4-dihydro-1H-isochromene-1-carboxylic acid (9.10 g, 35.4 mmol) and CDI (4.14 g, 42.5 mmol) in 200 mL of dry DCM was stirred at r.t. for 30 min and then O,N-dimethyl-hydroxylamine (5.99 g, 42.5 mmol) was added. The resulting mixture was stirred overnight. The solvents were removed under vacuum, and the residue was purified with silica gel column chromatography to give 5-bromo-N-methyl-N-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxamide. 1H-NMR (400 MHz, CDCl3) δ 7.40 (d, J=8.0 Hz, 1H), 6.99 (t, J=8.0 Hz, 1H), 6.93 (d, J=8.0 Hz, 1H), 5.63 (s, 1H), 4.23˜4.28 (m, 1H), 3.87˜3.92 (m, 1H), 3.71 (s, 3H), 3.19 (s, 3H), 2.71˜2.87 (m, 2H).

Provenance & Evidence