Benzyl Bromide → HCID 86727482, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-hydroxy-4-methyl-6-nitro-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.2 g, 0.72 mmol) and K2CO3 (0.30 g, 2.16 mmol) in DMF (10 mL) was added benzyl bromide (0.37 g, 2.16 mmol) dropwise. The solution was heated at 70° C. for 14 h. The reaction mixture was cooled to ambient temperature and brine (30 mL) was added. The aqueous phase was extracted with EtOAc (3×15 mL) and the combined organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 50% EtOAc in petroleum ether) to give 7-benzyloxy-4-methyl-6-nitro-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.140 g, 53%) as yellow solid. 1H NMR (CDCl3, 400 MHz): δ 8.08 (s, 1H), 7.62 (s, 1H), 7.49 (m, 2H), 7.44 (m, 2H), 7.39 (m, 1H), 6.81 (s, 1H), 5.23 (s, 2H), 4.70 (m, 3H), 1.56 (d, J=6.8 Hz, 3H).

Provenance & Evidence