6-Chloro-5-nitropyridine-2-carboxylic acid

2-Chloro-6-methyl-3-nitropyridine (97 g, 560 mmol) was slowly added to a flask previously charged with 18 M HSynthesis of the compound 27 The compound 26 (5 g, 0.029 mol) was dissolved in a concentrated sulphuric acid (10 mL) with agitation, a sodium dichromate (11.7 g, 0.039 mol) was added slowly in batches into the system, and the reaction was run at 30°C for 40 h. The above reaction liquid was added slowly into broken ice (300 g). A large amount of a white precipitate was precipitated, filtrated under reduced pressure, and vacuum-dried to obtain 3.8 g of a white product with a yield of 70percent. The melting point is 187.5-189.5 °C (water).In a reaction tube 6-chloro-5- nitropyridine-2-carboxylic acid (203 mg, 1.0 mmol), phenol (1 13 mg, 1.2 mmol) and dry powdered Cs2C03 (1, 042 mg, 3.2 mmol) were mixed in DMSO (2 ml.) and the resulting mixture was stirred at rt for 12 h. The reaction was monitored by LCMS and after completion it was diluted with water (20 ml_), sat NaHC03 (5 ml.) and EtOAc (25 ml_). The organic layer was separated and discarded. The aq layer was acidified to pH 4-5 using 1 N HCI and then extracted with DCM (3x30 ml_). The combined DCM layers were washed with brine (10 ml_), dried (Na2S04), and concentrated to provide the crude product which was used in the next step without purification. Yield: 230 mg (88%). LCMS [M+H]+ m/z 261.In a reaction tube 6-chloro-5- nitropyridine-2-carboxylic acid (203 mg, 1.0 mmol), cyclopropanol (70 mg, 1.2 mmol) and dry powdered Cs2C03 (1042 mg, 3.2 mmol) were mixed in DMSO (2 ml.) and the resulting mixture was stirred at rt for 12 h. The reaction was monitored by LCMS and after the completion it was diluted with water (20 ml_), sat NaHC03 (5 ml.) and EtOAc (25 ml_). The organic layer was separated and discarded. The aq layer was acidified using 1 N HCI (pH 4-5) and then extracted with DCM (3x30 ml_). The combined organic layer was washed with brine, dried (Na2S04) and concentrated to provide crude product which was used in the next step without purification. Yield 180 mg (79%). LCMS [M+H]+ m/z 225.In a reaction tube under N2 atmosphere

Molecular Weight:202.55
XLogP3:1.5
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