2-CHLORO-3-NITROPYRIDIN-4-OL

To a solution of 2 , 4-dichloro-3-nitropyridine (100 g, 518 mmol) in N, iV-dimethylformamide (500 mL) was added sodium acetate (106 g, 1295 mmol) at room temperature. The mixture was stirred at 120°C for 5 hours. The reaction completion was confirmed by TLC, then the mixture was cooled to room temperature and diluted with water (500 mL) followed by aqueous 2N HC1 solution to adjust the pH < 4. The aqueous layer was extracted with ethyl acetate (5 x 750 mL) . The combined organic layers were washed with brine, dried over sodium sulfate and under vacuum to give a crude product. The crude product was triturated with water, and the resulting solid was collected by filtration, and dried under vacuum to give the title compound (63 g, 65percent). MS(ESI)m/z: 175.1 (M+l); [0715] To a solution of XIV-2 (10 g, 52.1 mmol) in DMF (60 mL) was added NaOAc (10.3 g, 125 mmol), the reaction mixture was stirred at 120° C. for 3 hrs. The mixture was cooled to rt and poured into water, extracted with EtOAc. Combined organic phase was washed with brine and concentrated under vacuum to afford the crude product. The residue was purified by column chromatography (PE:EA=1:1) to afford XIV-3 as a pale yellow solid (5.4 g, 60percent yield). To a solution of XIV-2 (10 g, 52.1 mmol) in DMF (60 mL) was added NaOAc (10.3 g, 125 mmol), the reaction mixture was stirred at 120°C for 3 hrs. The mixture was cooled to rt and poured into water, extracted with EtOAc. Combined organic phase was washed with brine and concentrated under vacuum to afford the crude product. The residue was purified by column chromatography (PE:EA=1:1) to afford XIV-3 as a pale yellow solid (5.4 g, 60percent yield). ‘HNMR (CD3OD, 300MHz) ö 8.14 (d, J=6.0 Hz, 1H), 6.98 (d, J=6.0Hz, 1H).

Molecular Weight:174.54
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:173.9832197
Monoisotopic Mass:173.9832197
Topological Polar Surface Area:74.9
Heavy Atom Count:11
Complexity:276
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes