5-BROMO-3,4-DIHYDROQUINOLIN-2(1H)-ONE

A triphasic mixture of sodium azide (18.5 g, 284 mmol), sulfuric acid (18.8 M, 4.8 mL, 90 mmol), water (36 mL) and chloroform (144 mL) was stirred at 0°C for 2.5 h. The layers were separated and the organic layer was dried over sodium sulfate and filtered. The filtrate was added to a solution of 4-bromoindan-l-one (12.0 g, 56.9 mmol) in chloroform (215 mL). To this solution was added sulfuric acid (18.8 M, 18.7 mL, 351.6 mmol) dropwise over 10 min. The reaction mixture was stirred at 45°C for 4 h, then cooled to room temperature and stirred for 20 h. The mixture was poured onto ice (200 g) and neutralized by addition of 10percent aqueous sodium hydroxide (50 mL). The layers were separated and the aqueous layer was extracted with chloroform (100 mL). The combined organic layers were dried over sodium sulfate and evaporated. The crude product was recrystallized from ethanol (55 mL) to give the title compound (8.65 g, 38.2 mmol, 67percent) as an off-white powder. LCMS: 98percent, Rt 1.290, ESMS m/z 226 (M+H)

Molecular Weight:226.07
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:224.97893
Monoisotopic Mass:224.97893
Topological Polar Surface Area:29.1
Heavy Atom Count:12
Complexity:195
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes