7-Hydroxy-1,2,3,4-tetrahydroquinoline

7-Hydroxy-3, 4-dihydroquinolin-2(1H)-one(2.00 g, 12.26 mmol) was dissolved in THF (20 mL) and cooled to 0oC. After the addition ofNaBH4 (1.07 g, 28.19 mmol), I2 (3.42 g, 13.48 mmol) dissolved in THF (20 mL) was added to thesolution dropwise via an addition funnel. The reaction was then fitted with a condenser andrefluxed overnight. The solution was then neutralized with 3 M hydrochloric acid and thenextracted with dichloromethane three times, dried over magnesium sulfate. Evaporation ofthe solvent resulted in a viscous yellow oil. The crude material was purified by flash columnchromatography to yield the product as a white crystalline solid (1.80 g) in a 98percent yield.A solution of 7-hydroxy-3, 4-dihydroquinolin-2(1H)-one (12, 5.0 g, 30.64 mmol) in anhydrous THF (30 mL) was added dropwise to a suspended solution of LiAlH4 (1.7 g, 44.80 mmol) in anhydrous THF (70 mL) at 0. After the mixture was stirred for 15 min, the cooled batch was removed, and then the mixture was heated to 65 and stirred for 16 h. The resulting reaction mixture was diluted with THF (50 mL) and quenched with saturated NH4Cl (5 mL) in the ice-water batch. The aqueous solution was adjusted to PH 4-5 with 4 N HCl solution and extracted with EtOAc (100 mL × 2). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate/petroleum ether (1:20-1:10-1:5, v/v), to afford the intermediate 13 (3.03 g, 66percent yield) as a slight yellow solid. 1H NMR (400 MHz, CDCl3) δ 6.79 (d, J = 8.1 Hz, 1H), 6.12 (dd, J = 8.1, 2.3 Hz, 1H), 5.97 (d, J = 2.2 Hz, 1H), 4.55 (s, 2H), 3.32-3.13 (m, 2H), 2.67 (t, J = 6.4 Hz, 2H), 1.97-1.80 (m, 2H). 13C NMR (101 MHz, CDCl3) δ 154.68 (s), 145.50 (s), 130.45 (s), 114.45 (s), 104.79 (s), 101.18 (s), 42.04 (s), 26.32 (s), 22.46 (s).1, 2, 3, 4-tetrahydro-7-hydroxyquinoline 1, 2, 3, 4-tetrahydro-7-hydroxyquinoline 1, 2, 3, 4-tetrahydro-7-hydroxyquinoline. 1, 2, 3, 4-tetrahydro-7-hydroxyquinoline. 1, 2, 3, 4-tetrahydro-7-hydroxyquinoline

Molecular Weight:149.19
XLogP3:1.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:149.084063974
Monoisotopic Mass:149.084063974
Topological Polar Surface Area:32.3
Heavy Atom Count:11
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes