2-Chloro-5-nitro isonicotinic acid

2-chloro-4-methyl-5-nitropyridine (31 g, 180 mmol) was dissolved in conc.H2SO4 (300mL) and the resulting mixture was cooled to 0 °C. CrO3 (59.4 g, 594 mmol) was added to the solution. After stirring for 1 h at 0 °C, the mixture was warmed up to room temperature and stirred overnight. It was poured into ice-water (1 L). The mixture was warmed up to room temperature and filtered. The solid was then washed with water ( 2 L) and dried in vacuo to afford the desired product as a white solid (28.5g, 78percent); LC/MS: MS(ES) m/e 203 (MH=); 1H NMR (300 MHz, DMSO-d6) δ ppm 8.04 (s, 1 H), 9.16 (s, 1 H).(Step 1) 2-Chloro-5-nitro-pyridine-4-carboxylic acid (0167) (0168) 2-Chloro-4-methyl-5-nitro-pyridine (20.5 g, 119 mmol) was dissolved in concentrated sulfuric acid (200 ml), the resulting solution was cooled to 0° C., then chromium(VI) oxide (40.0 g, 400 mmol) was added thereto, and the resulting mixture was stirred at 0° C. for 1 hour and then at room temperature for 12 hours. The reaction liquid was diluted with water (2, 000 ml), and the precipitated solid was filtered and dried to obtain the title compound (18.0 g, 75percent). (0169) [00610] Step 1: To a solution of 2-chloro-4-methyl-5-nitro-pyridine (10.35 g, 60 mmol) in H2-Chloro-4-methyl-5-nitropyridine (20.5 g, 119 mmol) was dissolved in concentrated sulfuric acid (200 ml), and chromium trioxide (40.0 g, 400 mmol) was added thereto, followed by stirring at 0° C. for 1 hour. Then, the temperature was gradually raised from 0° C. to room temperature, followed by stirring for 12 hours. The reaction solution was poured into ice-water (2000 ml), and the temperature was raised from 0° C. to room temperature. The precipitated solid was filtered and dried under reduced pressure to obtain the title compound (18 g, 750). [0144] 2-chloro-4-methyl-5-nitropyridine (31 g, 180 mmol) was dissolved in conc.H2SO4 (300mL) and the resulting mixture was cooled to 0 °C. CrO3 (59.4 g, 594 mmol) was added to the solution. After stirring for 1 h at 0 °C, the mixture was warmed up to room temperature and stirred overnight. It was poured into ice-water (1 L). The mixture was warmed up to room temperature and filtered. The solid was then washed with water ( 2 L) and dried in vacuo to afford the desired product as a white solid (28.5g, 78percent); LC/MS: MS(ES) m/e 203 (MH=); 1H NMR (300 MHz, DMSO-d6) δ ppm 8.04 (s, 1 H), 9.16 (s, 1 H).(Step 1) 2-Chloro-5-nitro-pyridine-4-carboxylic acid (0167) (0168) 2-Chloro-4-methyl-5-nitro-pyridine (20.5 g, 119 mmol) was dissolved in concentrated sulfuric acid (200 ml), the resulting solution was cooled to 0° C., then chromium(VI) oxide (40.0 g, 400 mmol) was added thereto, and the resulting mixture was stirred at 0° C. for 1 hour and then at room temperature for 12 hours. The reaction liquid was diluted with water (2, 000 ml), and the precipitated solid was filtered and dried to obtain the title compound (18.0 g, 75percent). (0169) [00610] Step 1: To a solution of 2-chloro-4-methyl-5-nitro-pyridine (10.35 g, 60 mmol) in H2-Chloro-4-methyl-5-nitropyridine (20.5 g, 119 mmol) was dissolved in concentrated sulfuric acid (200 ml), and chromium trioxide (40.0 g, 400 mmol) was added thereto, followed by stirring at 0° C. for 1 hour. Then, the temperature was gradually raised from 0° C. to room temperature, followed by stirring for 12 hours. The reaction solution was poured into ice-water (2000 ml), and the temperature was raised from 0° C. to room temperature. The precipitated solid was filtered and dried under reduced pressure to obtain the title compound (18 g, 750). [0144]

Molecular Weight:202.55
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:201.9781343
Monoisotopic Mass:201.9781343
Topological Polar Surface Area:96
Heavy Atom Count:13
Complexity:229
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes