1,2,3,4-Tetrahydro-8-hydroxyquinoline

Pink crystals

The 100mmol 8-hydroxy quinoline and load 0.7mmol catalyst polymer microspheres [...] Poly (DVB-co-NVP) Rh and 500 ml of water are added in a reaction kettle, to hydrogen replaces the cauldron five times the air in, and then filled with hydrogen, the reaction at normal temperature and pressure 40 minutes, the aqueous phase is extracted three times with ethyl ether, the merger ether level, ethyl ether evaporate after drying, to obtain 8-hydroxy -1, 2, 3, 4-tetrahydro-quinoline, yield 95percent.Precatalyst (50 mg), NaBH4 (or NaBD4) (3e12 mmol), 1 mmol ofthe N-cyclic substrate and 5 ml deionized and degassed water (orD2O) were placed in a 25 ml three-necked flask equipped with areflux condenser and a pressure release valve to discharge thehydrogen gas self-generated during the reactions. The operationwas carried out under inert atmosphere. The reaction mixture wasvigorously stirred at different temperatures (25e60 C) for the timeselected. The complete conversion of substrate was determined bysubmitting small samples to spot thin layer chromatography (TLC).After completion, the slurry was centrifuged to separate the catalyst.The solid phase obtained was washed with deionized H2O andthen several times with ethyl acetate to remove all organic residue.The filtrate was collected, extracted with ethyl acetate and theextract dried over anhydrous MgSO4. After removal of the solvent invacuo, the corresponding product was obtained. In some cases, asilica-gel column chromatography was used to purify the product(isolated yield). The product analysis and identification was conductedby comparing the NMR spectral data with those of thepublished pure substances (all analyzed by 1H NMR and 13C NMRon Bruker Avance II 400 MHz spectrometer). The reaction selectivitieswere obtained from the NMR spectra by integration ofcharacteristic peaks for the product and reactant.General procedure: In a 1.5 mL reaction vial, B(C6F5)3 (0.025 mmol, 5.0 mol percent) was dissolved in chloroform (0.60 mL), towhich diethylsilane (1.75 mmol, 3.5 equiv) was added. After shaking briefly, quinolines (1a-p, 0.50 mmol, 1.0equiv) was subsequently added to the above catalyst solution under argon atmosphere. The reaction mixturewas stirred at 25-65

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