Nitroethane → HCID 69640425, compound

Participants

Reaction Steps

A stirred solution of 2,3-dihydro-1H-3a,4-diaza-cyclopenta[a]indene-8-carbaldehyde (2.3 g) and ammonium acetate (1.05 g) in nitroethane was heated to 100° C. for 2.5 h, cooled to room temperature, and evaporated under reduced pressure. The residue was partitioned between water and ethyl acetate, the phases separated, the aqueous phase re-extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane 2:1 to 4:1) to afford 8-(2-nitropropenyl)-2,3-dihydro-1H-3a,4-diaza-cyclopenta[a]indene as a yellow solid (2.4 g, 80%); MS (EI) 244 (M+H)+, 224, 195, 171; 1H NMR (δ, CDCl3) 8.31 (dd, 1H, J=1,5 Hz), 8.29 (s, 1H), 7.92 (dd, 1H, J=1,8 Hz), 7.16 (dd,1H, J=5,8 Hz), 4.34 (t,2H, J=6 Hz), 3.18 (t,2H, J=8 Hz), 2.72 (dt,2H, J=6,8 Hz), 2.45 (s,3H) ppm.

Provenance & Evidence