Bromine → HCID 15661170, compound

Participants

Reaction Steps

To a solution of 1 q (5.81 mmol) of 22 in 30 mL of qlacial acetic acid, heated at 100°, was added 300 μl of bromine in 3 mL glacial acetic acid. After the addition, the reaction mixture was heated at 100°-110° C. for 4 hours. The cooled reaction mixture was diluted with I00 mL of water and neutralized with aqueous sodium bicarbonate. The product crystallized from solution as a light yellow solid. Yield upon drying the collected solid Was 1.37 g (88%). Recrystallization from chloroform/hexane afforded analytically pure 23: mp 167°-170° C.; TLC (chloroform/methanol, [90:10]), Rf =0.56, IR(KBr pellet), 2949, 2929, 1581, 1521, 1482, 1461, 1448, 1418, 1291, 872 cm-1 ; 1H NMR (dimethyl sulfoxide-d6) δ71, and 7.43 (2 H, 2× s, aromatic protons), 4.04 (2 H, t, J~7 Hz, C(1) methylene), 2.91 (2 H, t, J~7 Hz), C(3) methylene), 2.59 (2 H, quintet, J~7 Hz, C(2) methylene), 2.39 (3 H, s, 7-methyl); mass spectrum (EI mode) m/z 250 and 252 (P+, 79Br and P+, 81Br), 171 (P+ -Br). Anal. Calcd for C11H11BrN2.0.25 H2O: C, 51.47; H, 4.31; N, 10.91. Found: C, 51.56; H, 4.24; N, 10.78.

Provenance & Evidence