8-Bromomethylquinoline

Light yellow powder

To an over-dried 300 mL three-necked flask, 8-methyl quinolone (10.0 g, 69.8 mmol), benzoyl peroxide (0.843 g, 3.49 mmol) and cyclohexane (150 mL) were added under a NNaH (0.135g, 3.38 mmol, 60percent) was washed with hexane (7 mL) and suspended in dry DMF (4 mL). To this suspension, isatin (0.33 g, 2.25 mmol) was added slowly over a period of 10 minutes in small portions and the sides of the reaction container were rinsed with 1.5 mL of DMF to wash in all of the isatin that stuck on the sides. After stirring for 20 minutes 8- (bromomethyl)quinoline (0.5 g, 2.25 mmol) was added. The reaction was stirred at room temperature for 3 h. TLC indicated completion of the reaction. Crushed ice was added over the solution and the precipitated solid was filtered, washed with excess water and dried under high vacuum overnight. The crude compound was dissolved in EtOAc by boiling to which a small amount of hexane was added. The solution was left for crystallization at room temperature for 4 h. The crystallized compound was filtered, washed with 50percent EtOAc/hexane, dried under suction and then under high vacuum overnight. Yield: 0.29g (45percent). ' NMR (400 MHz, CDC13) delta 9.01 (d, J = 4.2 Hz, 1H), 8.21 (d, J = 8.3Hz, 1H), 7.80 (d, J = 8.2Hz, 1H), 7.70 (d, J = 7.2 Hz, 1H), 7.60 (d, J = 7.4 Hz, 1H), 7.78 - 7.51 (m, 2H), 7.42 (t, J = 7.8 Hz, 1H), 7.02 - 7.07 (m, 2H) & 5.70 (s, 2H).

Molecular Weight:222.08
XLogP3:3.6
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:220.98401
Monoisotopic Mass:220.98401
Topological Polar Surface Area:12.9
Heavy Atom Count:12
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes