6-BROMO-2-CHLORO-QUINOLINE

White Crystalline Solid

Step 1 : A stirred solution of 6-bromoquinolin-2(1 /-/)-one (1.0 g, 4.4 mmol, 1.0 equiv) in phosphorous oxychloride (15 mL) was heated to 100°C for 15 h. The solvent was completely evaporated and water was added to the residue. The precipitated solid was filtered and dried under vacuum to obtain 6-bromo-2-chloroquinoline (1.0 g, 92 percent) as pink solid. LCMS (ES) m/z = 241.0, 243.0 [M+H]6-Bromo-2-chloroquinoline. The solution of the compound from Example 6 b)(3.Og, 13 mmol) in POCIPart C. Preparation of 6-bromo-2-chloroquinoline.; [00795] To phosphorus oxychloride (2.5ml, 26.8mmol) was added, in portions, the product from Part B(200mg, 0.893mmol). Refluxed for Ih, cooled to room temperature and poured onto crushed ice.Extracted with CHCl[00537] Part C. Preparation of -bromo-^-chloroquinoline.; [00538] To phosphorus oxychloride (2.5ml, 26.8mmol) was added, in portions, the product from Part B(200mg, 0.893mmol). Refluxed for Ih, cooled to room temperature and poured onto crushed ice.Extracted with CHCIExample A4; a. Preparation of intermediate 5; A mixture of 6-bromo-2 (lH)-quinolinone (0.089 mol) in POC13 (55 ml) was stirred at 60°C overnight, then at 100°C for 3 hours and the solvent was evaporated. The residue was taken up in CH2Cl2, poured out into ice water, basified with NHaOH concentrated, filtered over celite and extracted with CH2C12. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. Yield: 14. 5g of intermediate 5 (67percent).A mixture of 6-bromo-2(7H)-quinolinone (0.089 mol) in POClGeneral procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CHA solution of 6-bromoquinoline N-oxide (15.4 g, 68.75 mmol) in SOCIi (100 ml) was heated to refluxed for 6h and was cooled to R.T. SOCI

Molecular Weight:242.50
XLogP3:3.4
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