N,N-Diethylaniline → HCID 59458015, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 10 (500 mg, 2.31 mmol) and N,N-diethylaniline (1 ml, 1.5 eq) in 1,4-dioxane (20 ml) at 0° C. was added dropwise a solution of p-nitrobenzoylchloride (429 mg, 12.31 mmol). The reaction mixture was stirred at 20° C. for 2 h. TLC and mass spectrum showed still presence of 10. Therefore more p-nitrobenzoylchloride (43 mg, 0.1 eq ) was added and stirred for 20 h. The resulting precipitate was filtered and washed with more 1,4-dioxane. The collected solid was stirred in aqueous NH3, filtered washed with water and dried to give essentially pure 11 (821 mg, 97%); mp (MeOH)>300° C.; 1H NMR [(CD3)2SO] δ 10.58 (s, 1 H, NH), 9.56 (s, 1 H, NH), 8.65 (d, J=2.5 Hz, 1 H, H-2′), 8.38 (d, J=8.9 Hz, 2 H, H-3,5), 8.20 (d, J=9.2 Hz, 2 H, H-2,6), 8.17 (d, J=9.1 Hz, 1 H, H-5′), 8.02 (dd, J=9.0, 2.6 Hz, 1H, H-4′), 6.45 (s, 1 H, H-5″), 6.15 (s, 2 H, NH2), 2.12 (s, 3 H, CH3); HRMS (FAB+) (M+1) m/z calc. for C17H16N7O3 (M+1) m/z, 366.1315, found 366.1314; Anal. calc. for C17H15N7O3: C, 55.9; H, 4.1; N, 26.8, found C, 55.6; H, 4.2; N, 26.8%.

Provenance & Evidence