6-Hydroxy-2(1H)-quinolinone

Off-White Solid

Quinoline-2,6-diol is a dihydroxyquinoline that is quinoline in which the hydrogens at positions 2 and 6 are replaced by hydroxy groups.

REFERENCE A suspension of 6-hydroxycarbostyril (300 g) and potassium carbonate (308 g) in dimethylformamide (2 liters) is heated with stirring at 70-80 C. for one hour. To the suspension is added N-(3-bromopropyl)phthalimide (498 g), and the mixture is further stirred at the same temperature for 9 hours. The reaction solution is poured into ice-water, and the precipitated crystals are collected by filtration, washed successively with water, ethanol and diethyl ether, and dried to give 6-(3-phthalimidopropoxy)carbostyril (410 g) as a white powder. 1 H-NMR (DMSO-d6) delta ppm: 2.00-2.18 (2H, m), 3.78 (2H, t, J=6 Hz), 4.04 (2H, t, J=6 Hz), 6.47 (1H, d, J=9.5 Hz), 6.97 (1H, dd, J=2.5 Hz, J=9 Hz), 7.10 (1H, d, J=2.5 Hz), 7.18 (1H, d, J=9 Hz), 7.78 (1H, d, J=9.5 Hz), 7.75-7.94 (5H, m), 12.08 (1H, brs)The above step product (24.6 g, 82.7 mmol) was added to a 500 mL three-neck flask and250 mL of toluene was cooled down to 0 C., 32.2 g (4.2 mmol) of B(C6F5) and 15.4 g (115.8 mmol) of anhydrous aluminum trichloride were added in portions, and the temperature was gradually raised to 90 C.After stirring for 2 hours, the reaction solution was poured into 800 mL of ice-hydrochloric acid solution.The pH was adjusted to 2-3 and stirred for 1 hour. The layers were separated and the organic layer remained.Acetic acid (49.6 g, 0.827 mol) was added dropwise to the resulting organic layer.A solution of 30% H2O2 (9.4 g, 82.7 mmol) was added dropwise at 0-10C.After completion of the dropwise addition, incubate at 0-10C for 1 hour and continue stirring at room temperature for 1 hour.The peroxide is quenched by adding sodium bisulfite solution and the organic layer is separated.It is washed once with saturated brine, and the organic layer is concentrated under reduced pressure.The crude solid was recrystallized from methanol to give 10.8 g of a white solid product6-Hydroxy-2(1H)-quinolinone, yield 80.7%, Mp>300C, purity 99.2%.

Molecular Weight:161.16
XLogP3:0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:161.047678466
Monoisotopic Mass:161.047678466
Topological Polar Surface Area:49.3
Heavy Atom Count:12
Complexity:225
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes