Acetic Acid → HCID 178451560, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-tert-butyl 6-methyl 5-oxo-3,4,5,10-tetrahydrobenzo[b][1,7]naphthyridine-2,6(1H)-dicarboxylate (0.55 g) and hydrazine hydrate (2.5 mL) in DMA (4 mL) was heated at 130° C. for 2.0 h, acetic acid (4 mL) was added and the mixture was stirred at 130° C. for another 6 hours. The reaction mixture was cooled to room temperature, then water (30 mL) and EtOAc (100 mL) were added. The organic phase was separated and then washed with aqueous NaHCO3 (2×10 ml) and brine (20 ml), dried with Na2SO4 and filtered. The organic phase was concentrated in vacuum to give the crude product, which was then recrystallized from MeOH to afford the product (110 mg, 21%) as a yellow solid. 1H NMR (DMSO-d6) δ 11.7 (s, 1H), 10.52 (s, 1H), 7.60 (t, 1H, J=8.0 Hz), 7.43 (d, 1H, J=8.0 Hz), 7.21 (d, 1H, J=8.0 Hz), 4.22 (s, 2H), 3.54-3.55 (m, 2H), 2.30-2.33 (m, 2H), and 1.40 (s, 9H). MS (ESI) m/e [M+1]+341.0.

Provenance & Evidence