4-Chloro-6-hydroxyquinoline

Synthesis of 2-((4-chloroquinolin-6-yl)oxy)acetonitrile: To a stirred solution of 4-chloro-6-methoxyquinoline (500 mg, 2.5 mmol) in DCM (10mL) was added aqueous HI (5 mL, 45 percent). The mixture was heated to 100 °C and stirred for 5 hours. The solution was allowed to cool to room temperature and water (20 mL) was added. The organic phase was separated, and aqueous phase was basified and extracted with DCM (30 mL×3). The organic phase was combined and washed with water and brine, then dried over NaA. 4-chloro-6-methoxyquinoline 4a (500 mg, 2.5 mmol) was dissolved in 10 mL of dichloromethane, and hydroiodic acid (45percent, 5 mL) was added dropwise. Upon completion of the addition, the reaction solution was heated to 100° C. and stirred for 5 hours. 20 mL of water was added to the reaction solution, and the organic phase was separated. The aqueous phase was added dropwise with saturated sodium carbonate solution to adjusted the pH to 89, and extracted with dichloromethane (30 mL×3). The organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound 4-chloroquinolin-6-ol 24a (300 mg, a white solid), which was used directly in the next step.4-chloro-6-methoxyquinoline 4a (500 mg, 2.5 mmol) was dissolved in 10 mL of dichloromethane, and hydroiodic acid (45percent, 5 mL) was added dropwise. Upon completion of the addition, the reaction solution was heated to 100° C. and stirred for 5 hours. 20 mL of water was added to the reaction solution, and the organic phase was separated. The aqueous phase was added dropwise with saturated sodium carbonate solution to adjusted the pH to 89, and extracted with dichloromethane (30 mL×3). The organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound 4-chloroquinolin-6-ol 24a (300 mg, a white solid), which was used directly in the next step. (0288) MS m/z (ESI): 328.3 [M+1]

Molecular Weight:179.60
XLogP3:2.5
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