Hydrazine hydrate (1:1) → 9-Amino-2,3-Methylenedioxy-5-[2-(N,N-Dimethylamino)Ethyl]-5H-Dibenzo[c,h][1,6]Naphthyridin-6-One

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Reaction Steps

To a solution of compound 5a (40 mg, 0.1 mmol) in ethanol (10 mL), Ra—Ni (˜50 mg) and then hydrazine hydrate (0.2 mL) were added and the reaction stirred at room temperature for 3 h. The catalyst was filtered through Celite and filtrate was concentrated in vacuo to provide 23 mg of a solid (61.1% yield); mp 300–301° C.; 1H NMR (CDCl3) δ 2.36 (s, 6H), 3.01 (t, 2H, J=6.6), 4.33 (s, 2H), 4.63 (t, 2H, J=7), 6.18 (s, 2H), 6.91(dd, 1H, J=2.2, 8.8), 7.46 (s, 1H), 7.45 (d, 1H, J=2.2), 7.83 (s, 1H), 8.30 (d, 1H, J=8.8), 9.35 (s, 1H); HRMS m/z calcd for C21H20N4O3H: 377.1614. found 377.1606.

Provenance & Evidence