6-CHLORO-1,2,3,4-TETRAHYDROQUINOLINE

6-chloroquinoline (0.3 mmol, 49 mg)Tetrahydroxy diboron (0.9mmol, 81mg), Cu (OAc) 2 (0.015 mmol, 2.5 mg) was added to 1 mL of acetonitrile, 40 ° C for 12 hours, The residue was purified by thin layer chromatography to give 47.6 mg of 6-chloro tetrahydroquinoline in 95percent yield, 98percent purity, General procedure: A 20 mL Schlenk tube was charged with quinoline (1a; 65 mg, 0.5 mmol), Cu(OAc)2 (4.5 mg, 0.025 mmol), B2(OH)4 (135 mg, 1.5 mmol), and MeCN (2.0 mL). The mixture was stirred at 40 °C for 8 h until the reaction was completed (TLC), then cooled to room temperature and concentrated under reduced pressure. Water (10 mL) was added and the mixture was extracted with EtOAc (3 x 10 mL). The organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography with petroleum ether/ethyl acetate (8:1) as an eluent to give a brown liquid (2a: 65 mg, 98percent yield).To a solution of PdNPore (2.7 mg, 5 molpercent) in acetonitrile (5 mL) was added the substrate 6-chloroquinoline(81.8 mg, 0.5 mmol), hydrogen (5 bar), placed on a magnetic stirrer at 30 ° C for 16 h, column chromatography (silica gel, 200-300Methyl acetate) to give 6-chloro-1, 2, 3, 4-tetrahydroquinoline 69.57 mg in 83percent yield, General procedure: To a dry vial containing 8-methoxyquinoline, 1 (0.048 g, 0.3 mmol), Me2PhSiH (185 μL, 1.2mmol) and ethanol (70 μL, 1.2 mmol), Au/TiO2 (60 mg, 1.0 molpercent) was added. The Au contentin catalyst was ~1 wtpercent. The mixture was heated to 70 oC and the progress of reaction wasmonitored by TLC and GC. After 15 min (100percent conversion), ethanol (1 mL) was added and theresulting slurry was filtered under reduced pressure through a short pad of silica gel with the aidof ethanol (2-3 mL) to withhold the supported catalyst. The filtrate was evaporated undervacuum and the residue was chromatographed (n-hexane/ethyl acetate, 10:1) to afford 8-methoxy-1, 2, 3, 4-tetrahydroquinoline (1a) (41 mg, 84percent yield).To a solution of 6-chloroquinoline (1.5 g, 9.17 mmol) in CA flask filled with a mixture of 6-chloroquinoline (12.0 g, 73.3 mmol), PtO

Molecular Weight:167.63
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:167.0501770
Monoisotopic Mass:167.0501770
Topological Polar Surface Area:12
Heavy Atom Count:11
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes