2-Amino-6-chloro-3-nitropyridine

YELLOW POWDER

In the flask were poured into 500mL 200mL anhydrous ethanol at 0 ammonia gas was slowly passed through 2h, and then 4.8g (0.025mol) 2, 6- dichloro-3-nitropyridine (V) into the solution at room temperature stir overnight. The reaction is completed clear yellow solution was rotary evaporated to dryness under reduced pressure, ice water was added, filtered, washed with water and dried to give a yellow solid 2-amino-3-nitro-6-chloropyridine (I) 4.0g, 92percent yieldStep-1: Synthesis of Compound 2: Intermediate 4 6-Chloro-3-nitro-pyridin-2-ylamine To a solution of commercially available 2, 6-dichloro-5- nitropyridine (20.0 g, 95.3 mmol) in ethanol (300 mL) was added aqueous ammonia (60 mL), and the mixture was stirred at room temperature for 10 hours. The resulting precipitate was filtered, washed with ethanol, and dried in vacuo to give 6-amino-2-chloro-5-nitropyridine (13. [8 G, 83 percent). THE COMPOUND] thus obtained was suspended in an acetic acid solution (130 mL) of [30percent] hydrogen bromide. The suspension was stirred at [100°C] for 26 hours, cooled to room temperature, and concentrated in vacuo. The resulting residue was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue thus obtained [2, 6-Dichloro-3-nitropyridine, 25.0 gm (0.129 mole) was dissolved in methanol (50.0 ml) at room temperature. To a flask charged with 2, 6-dichloro-3-nitropyridine (3 g, 15.5 mmol) was added2M ammonia in isopropanol solution (18 ml, 36 mmol) and this mixture was stirredovernight at room temperature. The reaction was driven to completion by the addition ofammonia solution (aq). The resulting precipitate was filtered off, washed with water and then dried over vacuum for an hour. Intermediate 5 was isolated as a fluffy yellow powder (1.38 g, 51percent).LCMS (m/z): [IVIH] calcd. for C5H4C1N302, 173.56; found 174.00.A solution of 100 gm. 2, 6-dichloro-3-nitro-pyridine in 800 ml isopropyl alcohol is taken in round bottom flask. 300 ml of aqueous ammonia solution (20-25percent) is added at 20-25°C. The reaction mass is stirred for 20-24 hours at 20-25°C. After completion of the reactionThe solid is filtered and washed with 100 ml isopropyl alcohol then dried to obtain 70-75 gm 2-amino-3-nitro-6-chloro-pyridine.To a stirred solution of Compound 39a (50g, 261.78mmol) was added 38percent ammonia solution (150ml) and heated at 50°C for 5h. Upon completion, the obtained solids were filtered and given diethylether washings to afford the required compound as a yellow solid (30g).Gaseous ammonia was distilled through a cold (dry-ice) trap into a solution of 2, 6-dichloro-3- nitropyridine (9.65 g, 50 mmol) in anhydrous EtOH (100 mL), until the dichloro derivative was consumed (by TLC). The resultant solution was evaporated to dryness to afford a solid containing the title product and compound 4. Crystallization from iPrOH afforded the title product in pure form (65percent yield).

Molecular Weight:173.56
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:172.9992041
Monoisotopic Mass:172.9992041
Topological Polar Surface Area:84.7
Heavy Atom Count:11
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes