2-Amino-4-nitrobenzaldehyde

5.1.133 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).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).5.1.133 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).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).

Molecular Weight:166.13
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:166.03784206
Monoisotopic Mass:166.03784206
Topological Polar Surface Area:88.9
Heavy Atom Count:12
Complexity:190
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes