Carbon Dioxide → (z)-11-(3-(Dimethylamino)propylidene)-6,11-dihydrodibenz[b,e]oxepin-9-carboxylic acid

Participants

Reaction Steps

Pure (Z)-3-(9-bromo-6,11-dihydrodibenz[b,e]oxepin-11-ylidene)-N,N-dimethylpropylamine (0.78 g., 2.2 mmole), in cold (-70° C.) dry tetrahydrofuran (50 mL), was treated with 2.4 mmole n-butyl lithium in hexane followed by gaseous carbon dioxide by the procedure of Example I, Step c. This provided the desired carboxylic acid which was recrystallized from water to yield 0.15 g. pure Z-isomer, m.p. >205° C. (decomp.) with melting at 210° C. pmr (CDCl3 /D2O) δ: 7.84 (d, J=1.8 Hz, 1H, H10), 7.81 (dd, J=6.4, 1.8 Hz, 1H, Hg), 6.94-7.35 (m, 5H, aromatic), 5.78 (t, J=6.9 Hz, 1H, CH=), 5.25 (s, 2H, CH2O), 3.20 (m, 2H, NCH2), 2.80 (s, 6H, NMe2), 2.50-2.90 (m, 2H, CH2).

Provenance & Evidence