Ammonia → HCID 44549405, compound

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Reaction Steps

Powdered 205 (350 mg, 0.88 mmol) was added to stirred conc. H2SO4 (4 mL) at 0° C. and the mixture was warmed to room temperature for 20 min. The resulting solution of amine was cooled to −5° C. and treated dropwise with a solution of KNO3 (98 mg, 0.97 mmol) in conc. H2SO4 (1 mL). The mixture was stirred at 0° C. for a further 5 min, then poured into ice/water and neutralized with dilute aqueous NH3. The resulting solid was filtered off, dissolved in CH2Cl2, and the solution was filtered through a column of silica gel and evaporated to dryness. Recrystallization from CH2Cl2/i-Pr2O followed by EtOAc gave 1-(chloromethyl)-8-(methylsulfonyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole (206) (207 mg, 69%) as a red solid: mp 193-194° C.; 1H NMR [(CD3)2SO] δ 8.34 (d, J=1.5 Hz, 1H), 8.31 (d, J=9.1 Hz, 1H), 7.82 (s, 1H), 7.76 (dd, J=9.1, 1.9 Hz, 1H), 6.62 (br s, 1H), 4.37-4.28 (m, 1H), 3.93 (dd, J=11.1, 4.1 Hz, 1H), 3.87 (td, J=9.8, 2.3 Hz, 1H), 3.80-3.70 (1, 2H), 3.33 (s, 3H). Anal. (C14H13ClN2O4S) C, Ht N. The structure of 206 was confirmed by x-ray crystallography see FIG. 1.

Provenance & Evidence