Tert-Butyl nitrite → HCID 14168963, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of t-butylnitrite (0.027 g, 0.26 mmol) in anhydrous DMF was added 2,7-diamino-3-cyano-4-phenyl-4H-chromene (53 mg, 0.201 mmol) in one portion. The reaction was immediately immersed into a 65° C. oil bath. Gas evolution occurred slowly. After stirring at 65° C. for 1.5 h, the reaction was quenched with addition of water (5 mL), and extracted with EtOAc (3×10 mL). The EtOAc extracts were washed with brine (2×5 mL), dried over MgSO4, and evaporated. The red residue was purified by chromatography on silica gel with EtOAc and hexane (1:2) as eluant to yield 6 mg (12%) of the title compound as a light yellow solid. 1H NMR (CD3Cl, 300 MHz): 7.35–7.17 (m, 6H), 7.06–6.96 (m, 3H), 4.75 (s, 1H), 4.61 (brs, 2H).

Provenance & Evidence