3-Bromo-5-nitro-2(1H)-pyridinone

First step A solution of bromine (2.1 ml, 39.3 mmol) was added dropwise to a solution of compound 1 (5 g, 35.8 mmol) in 700 ml of water. The reaction medium was stirred at 5°C for 2.5 hours and then maintained at room temperature.The resulting precipitate was collected by filtration, washed with water and dried to give compound 2 (yellow solid, 7.25 g, yield: 93percent).The NMR analyses (1H 400 MHz DMSO-d6) are in accordance with the expected structure.Intermediate 5; 5, 6-diphenylpyridin-3-amineA. 3-Bromo-5-nitropyridin-2-olTo a solution of 5-nitropyridin-2-ol (0.06 mol, 8.6 g) in 400 ml of water at 40°, 3.7 ml of Br3-Bromo-2-methyl-5-nitropyridine Step 1: A mixture of 2-hydroxy-5-nitropyridine (50 g; 0.358 mol) and water (7 L) were warmed to 40° C. and bromine (21 mL; 0.393 mol) was added dropwise over 20 min. After stirring at 40° C. for 2.5 h, the mixture was cooled to 10° C. and the crude product was isolated by filtration. The solid was washed with water and dried in vacuo to give 70 g of 3-bromo-2-hydroxy-5-nitropyridine as a solid (90percent yield). mp 212-214° C. (with decomp); A mixture of 2-hydroxy-5-nitropyridine (50.0 g, 0.358 mol) and water (7 L) was warmed to 40° C. and bromine (21.1 mL, 0.393 mol) was added dropwise over 20 min. After stirring at 40° C. for 2.5 h, the mixture was cooled to 10° C. and the crude product was isolated by filtration. The solid was washed with water and dried in vacuo to give 3-bromo-2-hydroxy-5-nitropyridine as a solid (70.0 g, 90percent yield). mp 212-214° C. (with decomposition); Step 1: A mixture of 2-hydroxy-5-nitropyridine (50.0 g; 0.358 mol) and water (7 L) was warmed to 40° C. and bromine (21.1 mL; 0.393 mol) was added dropwise over -20 min. After stirring at 40° C. for 2.5 h, the mixture was cooled to 10° C. and the crude product was isolated by filtration. The solid was washed with water and dried in vacuo to give 70.0 g of 3-bromo-2-hydroxy-5-nitropyridine as a solid (90percent yield). mp 212-214 ° C. (with decomp); Into a 500 ml 3-necked roundbottom flask, was placed a solution of 5-nitropyridin-2-ol (50 g, 357.14 mmol, 1.00 equiv) in CH3CN (300 ml). To the above was added NBS (64 g) in several batches. The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at room temperature. A filtration was performed and the filter cake was collected. This resulted in 70 g (85percent) of 3-bromo-5-nitropyridin-2-ol as a white solid.Preparation of 3-bromo-5-nitropyridin-2-ol To a solution of 5-nitropyridin-2-ol (10 g, 0.06 mmol) in water was added Brto mixture ofaqueous solution (50ml) having 2-hydroxy-5-nitropyridine(50 mmol) slowly added into the bromine (60mmol)., after strrring for 2.5 h at 40

Molecular Weight:218.99
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:217.93270
Monoisotopic Mass:217.93270
Topological Polar Surface Area:74.9
Heavy Atom Count:11
Complexity:276
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes