* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With manganese(IV) oxide In dichloromethane at 20℃; for 23 h; Inert atmosphere
5.1.133 6,7-Didehydro-17-methyl-7'-nitroquinolino[2',3':6,7]morphinan-3,14β-diol hydrochloride (SYK-71) SYK-71 was prepared from compound 29c according to the procedure used to prepare SYK-27. Yield, 98percent; a yellow amorphous solid. Mp 247-249 °C (dec). Anal. Calcd for C24H23N3O4·1.0HCl·1.2H2O: C, 60.62; H, 5.60; N, 8.84. Found: C, 60.69; H, 5.61; N, 8.85.
86%
With manganese(IV) oxide In tetrahydrofuran; dichloromethane at 20℃; for 2 h;
A mixture of(2-amino-4-nitrophenyl)methanol (650 mg, 3.87 mmol) and manganese dioxide (1680 mg, 19.33 mmol) in THF (5 mL) and dichloromethane (25 mL) was stirred at room temperature for 2 h. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (40percent —* 50percent ethyl acetate in hexanes; 25g column) to afford 2-amino-4-nitrobenzaldehyde (550 mg, 86percent yield) as an orange solid: ‘H NMR (400MHz, DMSO-d6) ö 9.99 (s, 1H), 7.85 (d, J=8.6 Hz, 1H), 7.63 (d, J=2.3 Hz, 1H), 7.55 (br. s., 2H), 7.35 (dd, J=8.6, 2.3 Hz, 1H).
Reference：
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[2] Patent: WO2015/6100, 2015, A1, . Location in patent: Page/Page column 113
[3] Patent: EP2128157, 2009, A1, . Location in patent: Page/Page column 103
[4] Patent: WO2015/95795, 2015, A1, . Location in patent: Paragraph 0586
2
[ 528-75-6 ]
[ 109466-84-4 ]
Yield
Reaction Conditions
Operation in experiment
98 %Chromat.
With hydrogen In methanol at 100℃; for 6 h; Autoclave
General procedure: The hydrogenation of nitroarenes was carried out in a Teflon-lined stainless steel autoclave equipped with a pressure gauge anda magnetic stirrer. Typically, a mixture of 0.5 mmol nitroarene, 15molpercent Co/C–N–X catalyst, 100 L n-hexadecane and 2 mL solventwas introduced into the reactor at room temperature. Air in theautoclave was purged several times with H2. Then, the reactionbegan by starting the agitation (600 r/min) when hydrogen was reg-ulated to 1 MPa after the reaction temperature was reached. Afterreaction, the solid was isolated from the solution by centrifuga-tion. The products in the solution were quantified and identifiedby GC–MS analysis (Shimadzu GCMS-QP5050A equipped with a0.25 mm × 30 m DB-WAX capillary column).1H NMR and13C NMRdata were obtained on Bruker Avance III 400 spectrometer usingCDCl3or DMSO-d6 as solvent and tetrmethylsilane (TMS) as aninternal standard. The pure product in the scale-up experimentwas obtained by flash column chromatography (petroleum ether and ethyl acetate).
Reference：
[1] Chemische Berichte, 1904, vol. 37, p. 1873
[2] Recueil des Travaux Chimiques des Pays-Bas, 1920, vol. 39, p. 581
[3] Journal of Molecular Catalysis A: Chemical, 2016, vol. 420, p. 56 - 65
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
