7-Methoxyquinoline

Yellow Oil

To a solution of sodium hydride (5.5 g, 137.50 mmol, 60percent) in N, N-dimethylformamide (150 ml) was added quinolin-7-ol (8 g, 55.1 1 mmol). The reaction was stirred for 1 h at 0°C in a water/ice bath. Then CHTo a solution of quinolin-7-ol (5 g, 34.44 mmol) and Cs2CO3 (22.46 g, 68.89 mmol) in DMF (50 mL) was added iodomethane (2.1 mL, 34.44 mmol). The mixture was stirred at 20 °C for12 b under a nitrogen atmosphere. Water (100 mL) was added and the mixture was extracted with EtOAc (5OmL x 3). The combined organic layers were washed with brine (100 mE x 3), dried over anhydrous Na2SO4 and concentrated in vacuo. The cmde residue was purified by silica gel chromatography (petroleum ether EtOAc = 10: 1) to give the title compound (2.0 g, 25percent) as a yellow oil.In the reactor, 100 mg of substrate 7-methoxy-1, 2, 3, 4-tetrahydroquinoline, 10 mg of boron nitrocarbon photocatalyst, 3 mlOf ethanol and 1.2 equivalents of potassium carbonate, the reaction was stirred at room temperature light illumination 24h, after the reaction was extracted with ethyl acetate, combined with The organic phase was dried, filtered, and the solvent was distilled off under reduced pressure to give a crude product. The column was eluted with petroleum ether: 3: 1 by volume Ethyl acetate mixed solvent, yield 89percent.(a) 7-(Methyloxy)quinoline; A suspension of NaH (3.3g; 137.93mmol) in anhydrous DMF (160ml) was cooled to 0°C with stirring under argon. 7-Quinolinol (8g; 55.17mmol) dissolved in anhydrous DMF (320ml) was added and the mixture was stirred at 0°C under argon for Ih. The mixture was then allowed to warm to rt and MeI (7.8ml; 55.17mmol) was added and the reaction was stirred for Ih. Ice water was then added cautiously and the resulting mixture extracted with EtOAc (3 x 500ml). The organic layer from this extraction was then washed with water (400ml) and brine (400ml). The resulting organic layer was dried with MgSOSodium nitrobenzene sulfonic acid (3.9 g, 17.3 mmol) and methanesulfonic acid (10 ml) were placed in a 100 ml three-necked flask and stirred. 0.2 g (0.8 mmol) of iron (II) sulfate hydrate, and 3-methoxyaniline (3.09 mL) were added dropwise and the mixture was heated to about 120 ° C.6.3 g of glycerol was added and the reaction was carried out at 135 ° C. for 16 hours. After completion of the reaction, 10Approximately 100 mL of M aqueous NaOH solution was added and extracted with ethyl acetate. The organic layer was collected, dried over anhydrous magnesium sulfate, and the solvent was removed and purified by column chromatography to obtain 4.2 g of RL-0107 (yield: about 48percent).A solution of compound 2-2(12.5 g, 79 mmol) and Pt02 (l . lg, 4.8mmol) in MeOH (500 mL) was stirred at rt for 16 hrs under an atmosphere of H2. The reaction mixture was filtered through Celite.(R).545 and the filtrate was concentrated. The residue was purified by silica gel column chromatography (EtOAc/petroleum ether = 1/8 (v/v)) to give compound 2-3 (9.0 g, 78percent yield) as a yellow oil. LC-MS (ESI): mlz 164 [M+H]+; NMR (500 MHz, CDC13): delta 6.84 (d, J = 8.5 Hz, 1 H), 6.20 (dd, J, = 8.5 Hz, J2 = 2.5 Hz, 1H), 6.04 (d, J = 2.5 Hz, 1H), 3.73 (s, 3H), 3.26 - 3.28 (m, 2H), 2.69 (t, J = 6.5 Hz, 2H), 1.91 (dd, Ji = 6.5 Hz, J2 = 4.5 Hz, 2H) ppm.To a solution of To a solution of Sodium nitrobenzene sulfonic acid (3.9 g, 17.3 mmol) and methanesulfonic acid (10 ml) were placed in a 100 ml three-necked flask and stirred. 0.2 g (0.8 mmol) of iron (II) sulfate hydrate, and 3-methoxyaniline (3.09 mL) were added dropwise and the mixture was heated to about 120 C.6.3 g of glycerol was added and the reaction was carried out at 135 C. for 16 hours. After completion of the reaction, 10Approximately 100 mL of M aqueous NaOH solution was added and extracted with ethyl acetate. The organic layer was collected, dried over anhydrous magnesium sulfate, and the solvent was removed and purified by column chromatography to obtain 4.2 g of RL-0107 (yield: about 48%).

Molecular Weight:159.18
XLogP3:2.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:159.068413911
Monoisotopic Mass:159.068413911
Topological Polar Surface Area:22.1
Heavy Atom Count:12
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes