4-NITRO-PYRIDIN-2-YLAMINE

Step 3: 4-nitropyridin-2-am-ne Intermediate-22 [00194] N-(4-methoxybenzyl)-4-nitropyridin-2-amine (Int-21 , 27.8 g, 0.11 mol) and anisole (13 mL, 0.12 mol) were dissolved in trifluoroacetic acid (1 12 mL) and heated at 80 °C for 2 h. The reaction mixture was allowed to cool to rt and concentrated. Trituration of the resulting residue with EtOAc and hexanes produced a light yellow solid that was isolated via filtration. The filtrate was allowed to stand overnight and a second crop of crystals was obtained. The combined batches of solids were dissolved in IN NaOH (250 mL) and extracted with EtOAc (2 x 250 mL). The combined organic solutions were dried over magnesium sulfate, filtered and concentrated to give 4-nitropyridin-2-amine as an orange solid (10.2 g, 67percent). LCMS: (FA) ES+ 140; NMR (400 MHz, CDStep 3:[0062] Step 3: To N-[(4-(methoxyphenyl)methyl]-4-nitro-pyridin-2-amine (4.2g, 16.2 mmol) in toluene solution (10 mL) was added dropwise TFA (5.0 mL) at room tempreature. Then, the mixture was stirred at 80°C for reacting for 2 hours. TLC (PE:EA=1:1) showed that the reaction was completed. The mixture was concentrated under reduced pressure to remove the solvent. The residue was diluted with H2O (50 mL) and pH thereof was adjusted with solid NaHCO3 to neutral. The water phase was extracted with EA (50 mL33). The combined organic phase was dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified through column chromatography (silicon dioxide, petroleum ether/ethyl acetate=1/0∼1:1) to give 4-nitropyridin-2-amine (700 mg, 5.0 mmol, 31.1percent yield) as an orange solid compound. MS (ESI) Calcd. for C5H5N3O2 139, Found 140 [M+H]+.

Molecular Weight:139.11
XLogP3:0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:139.038176411
Monoisotopic Mass:139.038176411
Topological Polar Surface Area:84.7
Heavy Atom Count:10
Complexity:133
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes