Nitric Acid → HCID 46205076, compound

Participants

Reaction Steps

To a cooled solution of 4a (149 mg, 0.93 mmol) in concentrated sulfuric acid (4 mL), was added nitric acid (155 μl, d=1.38). After being stirred for 3 h at room temperature, the solution is crushed on ice (10g), made basic by the addition of aqueous saturated Na2CO3 solution (45 mL) and extracted with CH2Cl2. The organic layers were dried (MgSO4), filtered and evaporated to dryness to give 4m (171 mg, 90%); mp 182-184° C.; IR (KBr) 1698, 1380, 1134 cm−1; 1H NMR (400 MHz, CDCl3) δ 2.95 (s, 3H), 7.40 (t, 1H, J=7 Hz), 8.21 (d, 1H, J=7 Hz), 9.66 (d, 1H, J=7 Hz), 10.83 (s, 1H); 13C NMR (100 MHz, CDCl3) δ 17.4, 115.7, 123.4, 130.3, 130.4, 131.9, 144.3, 152.0, 187.3; MS m/z 205 (M+, 31), 177 (100), 104 (40), 78 (37), 51 (33).

Provenance & Evidence