Ethanol → HCID 135542469, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 8 (1.33 g, 3.40 mmol), ethanol (15 ml), and water (3.1 ml) was cooled in an ice-bath, then 30% aqueous H2O2 solution (2.8 ml) was added followed by granulated sodium hydroxide pellets (0.230 g, 5.78 mmol). The reaction mixture was stirred at ˜0° C. for 10 min, then it was placed in an oil bath preheated to 55° C. and stirred at this temperature for 40 min. The reaction mixture was allowed to cool to room temperature, then the solvents were removed in vacuo and the residue was suspended in water (˜40 ml). The pH of this mixture was adjusted to ˜5 with 1N hydrochloric acid. The white precipitate was collected by filtration, washed with water, dried in vacuo over P2O5, then it was triturated with ether, collected by filtration and dried in vacuo. The title compound 9 was obtained as a white solid 1.11 g (83%), m.p. 277-281° C. (it melts with decomposition), (Found: C, 70.22; H, 6.43; N, 10.65; C23H25N3O3 requires C, 70.57; H, 6.44; N, 10.73%); δH ((CD3)2SO) 1.50 (9H, s, C(CH3)3), 2.31 (3H, s, Me), 1.87, 2.55 (each 1H, m, 7-H), 2.97 (2H, m, 8-H), 5.15 (1H, q, J 7.50, 6-H), 6.77 (2H, d, J 8.6, 3′,5′-H), 6.91 (1H, d, J 8.70, N10—H), 7.44, 7.87 (each 1H, s, 5-H, 9-H), 7.66 (2H, d, J 8.75, 2′,6′-H); m/z ESI) 783 {(2M+H)+, 100%}, 392 {(N+H)+, 30%}, 199 (90).

Provenance & Evidence