Iodine → 8-nitro-2,3-dihydropyrano[3,2-e]isoindol-1(7H)-one

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2,3-dihydropyrano[3,2-e]isoindol-1(7H)-one ((71) 2.3 g, 12.3 mmol) in N-methylpyrrolidine (150 ml) and H2O (3 ml) was added NaNO2 (3.4 g, 49.2 mmol) in portions. To the mixture cooled at 0° C. was added iodine (9.4 g, 36.9 mmol). The reaction mixture was stirred for 3 hr, then quenched with 58% NaHSO3 (12 ml), H2O (12 ml), followed by addition of another 30 ml of 58% NaHSO3 solution. The solid was participated, filtered, and washed with H2O. The desired compound was air-dried under vacuum to give the title compound (2.41 g, 84%) as a yellow solid. MS (ES) m/z 233.2.

Provenance & Evidence