6-broMo-4-hydroxyquinolin-2(1H)-one

7B. 6-Bromo-4-hydroxy-lH-qumolin-2-one: To 7A (2.8g, 9.8 mmol) in methanol/water (30 mL/10 mL) was added sodium carbonate (1.55g, 14.6 mmol) and the mixture was stirred at rt for 3 days. The reaction mixture was added slowly to a stirred solution of aq. 1.0 N HCl (150 mL). The resulting white precipitate was collected by filtration. The solid cake was washed thoroughly with water and then dried under vacuum to give 2.57g (100percent) of the acid. MS 259.9 (M+2+H)Step 3: 6-bromo-4-hydroxyquinolin-2(lH)-one The product of Step 2 (14.7 g) was added to polyphosphoric acid (55.3 mL) and mixture was heated to 140°C for 3 hrs. The reaction mixture was cooled slightly and poured into 3N HC1 (168 mL). The pH was adjusted to 4 with 3N NaOH and resulting solid was filtered after cooling the reaction mixture to 10°C. The cake was washed with water and then slurried in 400 mL of 50percent isopropanol/water for 18 hours. The solids were filtered, air dried to give a pasty solid which was dried in vacuo at 90°C for 4 hours, ground in mortar/pestle and re-dried at 90°C for another 18 hours to give 15 g of the desired product.The product of Step 2 (14.7 g) was added to polyphosphoric acid (55.3 mL) and mixture was heated to 140° C. for 3 hrs. The reaction mixture was cooled slightly and poured into 3N HCl (168 mL). The pH was adjusted to 4 with 3N NaOH and resulting solid was filtered after cooling the reaction mixture to 10° C. The cake was washed with water and then slurried in 400 mL of 50percent isopropanol/water for 18 hours. The solids were filtered, air dried to give a pasty solid which was dried in vacuo at 90° C. for 4 hours, ground in mortar/pestle and re-dried at 90° C. for another 18 hours to give 15 g of the desired product.

Molecular Weight:240.05
XLogP3:1.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:238.95819
Monoisotopic Mass:238.95819
Topological Polar Surface Area:49.3
Heavy Atom Count:13
Complexity:264
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes