4-BROMO-ISOQUINOLINE2-OXIDE

13A. 13A. 2d) 4-BROMO-1-CHLORO-ISOQUINOLINE To a solution of 4-bromoisoquinoline (52. 08 g, 0. 250 MOL) in methylene chloride (600 mL) is added m-chloroperbenzoic acid (64.47 g, 0.250 MOL). The mixture is stirred for 2.5 hours. To the mixture is added 1.5 g of m-chloroperbenzoic acid and the mixture is stirred for 30 minutes. The solution is washed with 1 N NAOH, brine, and then dried over sodium sulfate. The solvent is removed to give a white solid. The solid is crystallized from hot acetone to yield 32.22 g (57.6percent) of a white SOLID. 1H, 13C NMR consistent with structure. The N-oxide (15.75 g, 0.0703 mol) is dissolved in chloroform (50 mL) and cooled in an ice bath. Phosphorus OXYCHLORIDE (20 mL) is added dropwise and then the mixure is warmed to room temperature and then heated to reflux for 1.5 hours. The mixture is allowed to cool to room temperature and is then poured over ice. The aqueous mixture is neutralized to pH 7-8 with NAHCO3 AND then extracted with chloroform. The organic phase is washed with brine, dried over sodium sulfate and the solvent is removed. The residue is purified by flash chromatography (SIO2/5percent ETHYL acetate/hexanes). Collected 12.22 g (72percent). M+H = 389. 'H NMR ; 5 8. 50 (s, 1H), 8.40 (d, 1H), 8.20 (d, 1H), 7.92 (t, 1H), 7.79 (t, 1H).A.

Molecular Weight:224.05
XLogP3:1.8
Hydrogen Bond Acceptor Count:1
Exact Mass:222.96328
Monoisotopic Mass:222.96328
Topological Polar Surface Area:25.5
Heavy Atom Count:12
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes