Tert-Butyl nitrite → HCID 10059873, compound

Participants

Reaction Steps

To a three-neck RB flask equipped with a thermometer and a condenser containing anhydrous DMF (1 mL) at 65° C. was added tert-butylnitrite (0.4 mL, 3.02 mmol), followed by slow addition of 3-cyano-2,7-diamino-4-phenyl-4H-chromene (263 mg, 1.0 mmol) in anhydrous DMF (1 mL) in 10 min. The reaction was stirred further for 5 min, then quenched with addition of water (10 mL). The mixture was extracted with EtOAc (3×10 mL). The EtOAc was washed with water (5 mL), brine (5 mL), dried over MgSO4, and evaporated. The red residue was purified by chromatography on silica gel with EtOAc and hexane (1:4) as eluant to yield 64 mg (26%) of the product as an off-white solid. 1H NMR (CDCl3): 7.4-7.18 (m, 7H), 7.07-7.01 (m, 2H), 6.96-6.62 (m, 1H), 4.77 (s, 1H).

Provenance & Evidence