Ethyl 8-Azido-4-Oxo-4H-Quinolizine-3-Carboxylate → Ethyl 8-Amino-4-Oxo-4H-Quinolizine-3-Carboxylate

Beteiligte Stoffe

Reaktionsschritte

A suspension of ethyl 8-azido-4-oxo-4H-quinolizine-3-carboxylate (14) (253 mg, 1.0 mmol) and 20 mg 5% Pd on carbon in 15 ml ethanol was stirred under ambient hydrogen pressure. The color of the reaction mixture rapidly changed from deep red to dark yellow. After 30 ml of hydrogen was absorbed by the reaction mixture, the catalyst was filtered off and the solvent was evaporated to give ethyl 8-amino-4-oxo-4H-quinolizine-3-carboxylate (15) (221 mg, 94%) as a yellow green powder. M.p.>250° C. 1H NMR (δ, DMSO-d6): 1.23 (t, J=7 Hz, 3H), 4.13 (q, J=7 Hz, 2H), 6.23 (d, J=7 Hz, 1H), 6.53 (d, J=2 Hz, 1H), 6.79 (dd, J=2 Hz, J=7 Hz, 1H), 7.32 (s, 2H), 7.81 (d, J=8 Hz, 1H), 8.94 (d, J=7 Hz, 1H). MS: m/s 232.0837; required for C12H12NO3: 232.0848.

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