ChemicalBook CAS DataBase List 3-CHLORO-2-HYDROXY-5-NITROPYRIDINE

3-CHLORO-2-HYDROXY-5-NITROPYRIDINE synthesis

5synthesis methods

Product Name:3-CHLORO-2-HYDROXY-5-NITROPYRIDINE
CAS Number:22353-38-4
Molecular formula:C5H3ClN2O3
Molecular Weight:174.54

5418-51-9
434 suppliers
$12.72/1gm:

22353-38-4
168 suppliers
$9.00/250mg

Yield: 96%

Reaction Conditions:

Stage #1:5-nitro-2-hydroxypyridine with hydrogenchloride at 20;
Stage #2: with sodium chlorate at 50; for 1 h;

Steps:

3.1.1. 2-Hydroxy-3-chloro-5-nitropyridine (2)
2-Hydroxy-5-nitropyridine (200 g, 1.42 mol) was added portion wise to 800 ml of concentrated HCl under constant stirring and then heated to 50 C. To this was slowly added a solution of sodium chlorate (80.0 g, 0.75 mol) inwater. The reactionwas maintained at the same temperature for an additional hour, and then cooled to 0 C. The precipitate obtainedwas filtered,washed thoroughly with water and dried to give 2-Hydroxy-3-chloro-5-nitropyridine. Yield: 240 g, 1.37 mmol (96.0%). M.P.: 195 e197 C. 1H NMR (300 MHz, DMSO-d6): d 8.65 (d, 1H, J ¼ 2.5 Hz), 8.36 (d, 1H, J ¼ 2.5 Hz). 13C NMR (300 MHz, DMSO-d6): d 153.40, 144.29, 143.59, 135.08, 130.44. MS (ES): 175 (M þ H)þ.

References:

Bajare, Swapnil;Anthony, Jessy;Nair, Amrutha;Marita, Rosalind;Damre, Anagha;Patel, Dharmeshkumar;Rao, Chandrika;Sivaramakrishnan;Deka, Nabajyoti [European Journal of Medicinal Chemistry,2012,vol. 58,p. 355 - 360]