Pyridine → HCID 59457990, compound

Participants

Reaction Steps

4-Nitrobenzoic acid (4.3 g, 16.36 mmol) was suspended in SOCl2 (30 mL), 2 drops of DMF were added, and the mixture was refluxed for 1 h (until a clear solution was obtained). The reaction mixture was cooled to room temperature and excess SOCl2 was removed under vacuum. The resulting residue was dissolved in 1,4-dioxane and added to a suspension of A4 (3.0 g, 16.20 mmol) in 1,4-dioxane (300 mL) containing pyridine (8 mL). The reaction mixture was stirred 16 h at 50° C., and the solvent was then evaporated. The residue was stirred in dilute aqueous ammonia, and the resulting precipitate was filtered and crystallized from MeOH to give A5 (5.3 g, 79%): mp (MeOH) 219-222° C.; 1H NMR [(CD3)2SO] δ 10.63 (s, 1H, NH), 9.04 (s, 1H, NH), 8.37 (d, J=8.9 Hz, 2H, ArH), 8.24-8.18 (m, 4H, ArH), 7.81 (bs, 1H, ArH), 7.45 (d, J=8.5 Hz, 1H, ArH), 7.34 (t, J=8.0 Hz, 1H, ArH), 6.99-6.95 (m, 3H, ArH), 13C NMR [(CD3)2SO] δ 166.9, 164.0, 150.3, 149.4 (2×C), 149.1, 140.5, 139.6, 129.5 (2×C), 129.2, 123.5 (2×C), 123.4, 115.8, 114.6, 111.6, 109; HRMS (FAB+) calc. for C18H15N4O3 (M+1) m/z 335.1144, found 335.1154.

Provenance & Evidence