Nitric Acid → HCID 15230214, compound

Participants

Reaction Steps

A solution of 245 mg (0.97 mmol) of 23 in a 5 mL mixture of fuming nitric acid and concentrated sulphuric acid (4:1) was stirred in an ice bath for 10 min. The completed reaction was poured over cracked ice and the pH of resulting solution adjusted to 6.5 with aqueous sodium bicarbonate. Extraction of this solution with 3×50 mL portions of chloroform, drying the extracts (sodium sulfate), and then concentration afforded a yellow solid, 165 mg (57%). Recrystallization from chloroform/hexane afforded analytically pure material: mp 201°-203° C.; TLC (chloroform/methanol, [95:5]) Rf =0.61; IR(KBr pellet) 1537, 1517, 1449, 1413, 1383, 1374, 1342, 1297, 884, 860 cm-1 ; 1H NMR (dimethyl sulfoxide-d6) δ7.77 (1 H, s, aromatic proton), 4.15 (2 H, t, J~Hz, C(1) methylene), 2.99 (2 H, t, J~7 Hz, C(3) methylene), 2.67 (2 H, quintet, J~7 Hz, C(2) methylene); 2.52 (3 H, s, 7-methyl); mass spectrum (EI mode) m/z 295 and 297 (P+, 79Br and 81Br), 249 and 251 (P+ -NO2) Anal. Calcd for C11H10BrN3O2 : C, 44.60; H, 3.40; N, 14.18. Found: C, 44.83; H, 3.31; N, 14.07.

Provenance & Evidence