Sulfuric Acid → HCID 68692459, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 184 (314 mg, 0.75 mmol) in a mixture of conc. H2SO4 (4.5 mL) and water (0.5 mL) was stirred at 90° C. for 3 h, then cooled and diluted with water (80 mL). The solution was clarified by filtration and adjusted to pH 4 with aqueous NH3. The resulting precipitate was collected, dissolved in EtOAc and the solution was then filtered, concentrated under reduced pressure to a small volume and diluted with hexane to give 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-8-carboxylic acid (187) (226 mg, 95%) as a red solid: mp 205-208° C.; 1H NMR [(CD3)2SO] δ 13.3 (v br, 1H), 8.38 (d, J=1.3 Hz, 1H), 8.19 (d, J=9.1 Hz, 1H), 7.82 (dd, J=9.1, 1.6 Hz, 1H), 7.76 (s, 1H), 6.45 (s, 1H), 4.35-4.25 (m, 1H), 3.91-3.80 (m, 2H), 3.76 (dd, J=11.2, 8.5 Hz, 1H), 3.72 (dd, J=10.3, 2.8 Hz, 1H). Anal. C14H11ClN2O4) C, H, N.

Provenance & Evidence