3-BROMO-4-CHLOROQUINOLINE

To a stirred suspension of 3-bromo-1H-quinolin-4-one (10) (22.44 g, 0.10 mol) in acetonitrile (100 mL) phosphorus oxychloride (18.43 g, 0.12 mol) was added dropwise at room temperature. j00520j A 50 mL pressure reaction vessel charged with To a stirred solution of To a stirred suspension of 3-bromo-1H-quinolin-4-one (10) (22.44 g, 0.10 mol) in acetonitrile (100 mL) phosphorus oxychloride (18.43 g, 0.12 mol) was added dropwise at room temperature. The reaction mixture was refluxed for 7 h. After cooling to room temperature it was poured on crushed ice (400 mL) and the pH was adjusted to 9 with potassium carbonate solution (10%, 220 mL). The resulting precipitate was filtered off, washed with water, and dried in vacuo. The title compound was obtained as a brown solid (22.58 g, 93%), mp 182-188 C (lit., 31 mp 69-69, 5 C); 1H NMR (DMSO-d6, 400 MHz) delta 9.08 (s, 1H), 8.25 (dd, 1H, J=0.8, 8.4 Hz), 8.12 (d, 1H, J=8.0 Hz), 7.95-7.89 (m, 1H), 7.86-7.80 (m, 1H); 13C NMR (DMSO-d6, 400 MHz) delta 151.6, 146.5, 140.2, 130.9, 129.5, 129.2, 126.4, 124.0, 117.7; C9H5BrClN (242.50); LCMS (ESI+) m/z 242, 244 [M+H]+. Anal. Calcd for C9H5BrClN (242.50) C, 44.58; H, 2.08; N, 5.78. Found: C, 44.43; H, 2.09; N, 5.79.

Molecular Weight:242.50
XLogP3:3.5
Hydrogen Bond Acceptor Count:1
Exact Mass:240.92939
Monoisotopic Mass:240.92939
Topological Polar Surface Area:12.9
Heavy Atom Count:12
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes