2,6-DICHLORO-3-NITRO-4-AMINOPYRIDINE

Light Yellow to Beige Solid

B. 4-Amino-2, 6-dichloro-3-nitro-pyridine; Portions of 2, 6-dichloro-4-nitroamino-pyridine (example A, 67.0 g, 322 mmol) were dissolved in concen- trated sulphuric acid (320 ml). The rate of addition was adjusted so that an internal temperature of 40 °Cwas not exceeded. The reaction mixture was heated to 100 °C. After a period of 1 hour, a yellow solutionwas obtainned which was poured onto ice-water (3 litres). A pH-value of 9.5 was adjusted by addition of 6N sodium hydroxide solution (approximately 1.9 litres). A colourless suspension was formed which wasstirred for 30 minutes at room temperature. The precipitate was collected by filtration, suspended in water(4 litres), and stirring was continued for 30 minutes at room temperature. The title compound was isolatedby filtration and was dried in vacuo(50 mbar, 17 h, 50 °C). A colourless solid was obtained (75.3 g, quan- titative yield).(5)(5)Sulfuric acid (32 mL) was placed in a 250 mL round-bottomed flask fitted with a magnetic stir bar and an internal thermometer. Intermediate 11 (6.19 g, 29.7 mmol) was added portionwise (the internal temperature must remain below 40 °C). The mixture was heated to 100 °C for 1 h, poured into ice water (300 mL) and the pH of the solution was adjusted to 9.5 by addition of 6 N aq. NaOH solution (250 mL). The suspension was stirred for 30 min at rt. The precipitate was collected by filtration, suspended in water (150 mL) and stirred at rt for 30 min. The solid was collected by filtration and dried under high vacuum overnight to give 5.47 g of intermediate 12 (88 percent yield, off- white solid).Part B2, 6-Dichloro-4-nitraminopyridine (1.66 g, 7.98 mmol) was added to 11 niL of concentrated sulfuric acid, and the resultant solution was heated on a steam bath for 30 minutes. After cooling to room temperature, the solution was poured onto 28 g of crushed ice, resulting in the formation of a tan precipitate. The mixture was cooled in an ice bath, and concentrated ammonium hydroxide was added until pH 7 was reached. The resultant slurry was stored at -10 °C overnight. The precipitate was collected by filtration using a Buchner funnel, washed with ice cold water, and dryed under vacuum to provide 4-amino- 2, 6-dichloro-3-nitropyridine (1.30 g, 78percent yield) as a light tan solid. Part CIntermediate 2: 2, 6-Dichloro-3-nitro-4-pyridinamine Procedure Gl : 2, 6-Dichloro-3-nitropyridin-4-amine (X).; To 40 mL of concentrated H2, 6-Dichloro-pyridin-4-ylamine (2 g, 12.27 mmol) was dissolved in sulfuric acid (26 mL) at 0°C.

Molecular Weight:208.00
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:206.9602317
Monoisotopic Mass:206.9602317
Topological Polar Surface Area:84.7
Heavy Atom Count:12
Complexity:186
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes