Nitric Acid → HCID 11579837, compound

Participants

Reaction Conditions

Reaction Steps

To a cold mixture of 7-chloro-3,4-dihydropyrimido[1,2-a]indole-10(2H)-one (0.221 g, 1.00 mmol ) in concentrated H2SO4 (1 mL), was added fuming nitric acid (0.042 mL, 1.00 mmol ) drop-wise with cooling in a ice/brine bath (−10° C.). After stirring for 10 minutes the ice bath was removed and stirring continued for 1 hour at room temperature. Controlling the temperature with an ice bath, fresh fuming HNO3 (0.021 mL) was added. After stirring for an additional hour the mixture was added to ice and basified with concentrated NH4OH. The resulting yellow solid was filtered, dissolved in CH2Cl2 and filtered again. The filtrate was washed with H2O and the organic layer was separated and concentrated to give the title compound as a bright yellow solid (0.209 g, 79% yield). Anal. Calc'd for C11H8ClN3O3+0.2H2O: C, 47.60; H, 3.00; N, 14.87. Found: C, 47.58; H, 3.02; N, 14.85. NMR (300 Mz, DMSO-d6): consistent. MS: (ES+) m/z 266 [M+H] one chlorine pattern observed. m.p.: 152-165° C.

Provenance & Evidence