4-Bromo-1-chloroisoquinoline

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).General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH4-Bromoisoquinoline (34) (200 mg, 0.961 mmol), NaA mixture of 4-bromoisoquinolin-1-ol (1.4 g, 5.80 mmol) and POCl3 (8.9 g, 58.09 mmol, 10 eq) was heated to reflux with stirring. The progress of the reaction was monitored by LCMS and was found to be complete after 4 h. The reaction mixture was cooled to RT, quenched with ice-cold water (100 mL) and extracted with EtOAc (3 × 25 mL). The combined organic layers were washed with water (3 × 20 mL) followed by saturated aqueous NaHCO3 solution (30 mL) and brine (20 mL). The organic layer was dried over anhydrous sodium sulfate. Removal of solvent under reduced pressure afforded 1.3 g (87percent) of 4-bromo-1-chloroisoquinoline as a white solid.

Molecular Weight:242.50
XLogP3:3.8
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