2-Chloro-6-hydroxyquinoline

2-chloroquinolin-6-ol is a monohydroxyquinoline that is 6-hydroxyquinoline in which the hydrogen at position 2 is replaced by a chlorine. It is an organochlorine compound and a monohydroxyquinoline.

General procedure: To a cooled solution of aryl methyl ether ( 1.0 equiv.) in DCM (10 mL) was added BBrTo a solution of 2-chloro-6-methoxyquinoline (Intermediate 1) (2.00 g, 10.4 mmol) in anhydrous DCM (100 mL) was added BBrTo a solution of 2-chloro-6-methoxyquinoline (Intermediate 1) (2.00 g, 10.4 mmol) in anhydrous DCM (100 mL) was added BBrA solution of 2, 6-quinolinediol 10 (5 g) in POC13 (21 ml) and DMF (3.4 ml) is stirred for 12 h at room temperature, then heated for 1 h at 115 °C. The reaction is poured into water (100 ml) at 0 °C and neutralized with a 32 percent aqueous NH3 solution. The solid obtained by filtration is washed with acetone, and the resulting organic phase is evaporated to give 2-chloro-6-quinolinol 11 as a solid. No further purification is needed. Yield: 98 percent. MS (MH+) : 180.A mixture of 2, 6-quinolinediol (10.75 g, 66.7 mmol) was suspended in DMF (24 ml) and phosphorousoxychloride (47.6 g, 333 mmol) was added to the mixture at room-temperature. The temperature increased to 70 °C, the suspension turned into a brown solution that precipitated. Ice (0.5 kg) was added, followed by concentrated ammonia (100 ml). The crystalline product was filtered, washed with water and 11.5 g (96percent) was isolated.Synthesis of 114 1-bromo-2-(2-bromomethoxy)ethane (37. 0 muL, 0.3 mmol), 2-Chloroquinolin-6-ol(116 mg, 0.65 mmol) and potassium carbonate (96.7 mg, 0.7 mmol)Dissolved in DMF (2.5 mL)Keep reacting at 70C for 4h TLC tracking responseUntil the reaction is complete.After the reaction is over, The reaction solution is extracted with a toluene-water system.The filtrate was dried over magnesium sulfate, Concentrate under reduced pressure, Purification by column chromatography afforded compound 10 (red solid, 95.8%; ethyl acetate: petroleum ether=1:2).2-Chloroquinolin-6-ol ((253 mg, 1.1 mmol) was dissolved in dry THF, and then PPh3 (393 mg, 1.5 mmol) was added thereto in succession.Triethylene glycol (68.3 muL, 0.5 mmol)And DIAD (diisopropylazodicarboxylate, 294 muL, 1.5 mmol).The reaction was kept at room temperature for 4 h, TLC traced It should be until the reaction is complete. After completion of the reaction, the mixture was concentrated under reduced pressure and purified by column chromatography to obtain Compound 6 (red solid, 95.8%; ethyl acetate:dichloromethane=1:1).

Molecular Weight:179.60
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:179.0137915
Monoisotopic Mass:179.0137915
Topological Polar Surface Area:33.1
Heavy Atom Count:12
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes