4-Methoxy-beta-nitrostyrene → (Rac)-3-(4-methoxyphenyl)-3,4,5,6-tetrahydro-1h-azepino[5,4,3-cd]indol-6-one

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Reaction Steps

In a manner similar to that described for the preparation of Example Q, methyl indole-4-carboxylate and p-methoxy nitrostyrene were condensed and the resulting nitro alkane was reduced/cyclized to give, after recrystallization (CH2Cl2/MeOH/hexanes), (rac)-3-(4-methoxyphenyl)-3,4,5,6-tetrahydro-1H-axepino[5,4,3-cd]indol-6-one, 16.9 mh (50%) as a white solid: m.p. 221-223° C.; 1H NMR (300 MHz, d4—MeOH) δ 3.57 (br m, 5H), 5.15 (br s, 1H) 6.62 (m, 2H), 6.86 (m, 2H), 7.08 (app t, J=7.8 Hz, 1H), 7.11 (s, 1H), 7.37 (d, J=7.9 Hz, 1H), 7.73 (d, J=7.5 Hz, 1H). Anal. (C19H16N2O20.25 H2O) C, H, N.

Provenance & Evidence