4-Bromo-6-quinolinecarbonitrile

To a solution of (b) (12 g, 70.5 mmol) in DMF (75 ml) was added dropwise phosphorous tribromide (8 ml, 84.6 mmol) over five minutes (slightly exothermic). The reaction was allowed to cool to room temperature and was then diluted with ice water (100 ml) and stirred 1 hour then diluted with additional water (300 ml). The product was filtered off, washed with water and air dried to provide 14.3 g of product (87percent). MS (+ve ion electrospray) m/z 233 (MH+).A solution of quinolinone (b) [(12.] [0G, ] 70.5 mmol) in DMF (60 ml) was treated dropwise with phosphorus tribromide (8.0 ml, 84.6 mmol) over 10 minutes (exothermic). After allowing to stir and cool to room temperature, ice water (100 ml) was added and the mixture was stirred 30 minutes, then basified to pH8 by dropwise addition of 50percent [NAOH] with cooling. The resultant solid was filterd off, washed with water and air dried to afford a tan solid (14.3g, 87percent). MS (ES) [MLE] [234] (M + H) +.4-Oxo-1 , 4-dihydro-quinoline-6-carbonitrile (12.0 g, 70.5 mmol) in DMF (60 mL) was treated dropwise with phosphorous tribromide (8.0 mL, 84.6 mmole) over 10 minutes (exothermic). After allowing to stir and cool to room temperature, ice water (100 mL) was added and the mixture was stirred 30 minutes, then neutralized to pH=8 by dropwise addition of 50percent NaOH with cooling. The percipitate was filterd off, washed with water and air dried to afford the title compound as a tan solid (14.3 g, 87percent): LC/MS (ES) m/e 234(M+H)+

Molecular Weight:233.06
XLogP3:2.6
Hydrogen Bond Acceptor Count:2
Exact Mass:231.96361
Monoisotopic Mass:231.96361
Topological Polar Surface Area:36.7
Heavy Atom Count:13
Complexity:232
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes