ChemicalBook CAS DataBase List 2,3-Diamino-5,6-dichloropyridine

2,3-Diamino-5,6-dichloropyridine synthesis

7synthesis methods

Product Name:2,3-Diamino-5,6-dichloropyridine
CAS Number:97941-89-4
Molecular formula:C5H5Cl2N3
Molecular Weight:178.02

5409-39-2

97941-89-4

General procedure for the synthesis of 5,6-dichloropyridine-2,3-diamine from 2-amino-3-nitro-5-chloropyridine: 5-chloro-3-nitropyridin-2-amine (2000.0 mg, 11.52 mmol) and stannous chloride (8740.0 mg, 46.09 mmol) were added slowly in a reaction vial. Hydrochloric acid (20.0 mL) was then added and the reaction mixture was stirred at 80-100 °C for 0.5 hours. Upon completion of the reaction, the pH was neutralized by adjusting to 7 with saturated 1N aqueous sodium hydroxide solution and then extracted with ethyl acetate (200.0 mL). The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 90:10). The fraction containing the target product was collected and the solvent was evaporated under reduced pressure to give 5,6-dichloropyridine-2,3-diamine as an ivory-colored solid (1000.0 mg, 49% yield).1H-NMR (300 MHz, DMSO-d6) δ: 6.80 (s, 1H), 6.04 (s, 2H), 5.11 (s, 2H).

203794-33-6 Synthesis

203794-33-6
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97941-89-4
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Yield:97941-89-4 92%

Reaction Conditions:

with iron;ammonium chloride in ethanol;water at 60; for 3 h;

Steps:

1

To a solution of Compound 2 (36.2 g, 174 mmol) in ethanol (775 mL) and water (310 mL) were added iron (48.6 g, 870 mmol) and ammonium chloride (46.5 g, 870 mmol), and the reaction mixture was stirred at 60° C. for 3 hours. The reaction suspension was filtered with Celite, followed by washing with ethanol, and ethanol of the filtrate was removed under reduced pressure. The obtained residue was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure. To the residue was added hexane, followed by filtration. The obtained residue was washed with hexane to obtain Compound 3 (28.46 g, 92%) as a brown solid. [0625] Compound 3; ¹H-NMR (DMSO-d6) δ: 5.10 (s, 2H), 6.02 (s, 2H), 6.82 (s, 1H).

References:

US2013/184240,2013,A1 Location in patent:Paragraph 0621; 0624; 0625

5409-39-2 Synthesis

5409-39-2
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$6.00/250mg

97941-89-4
44 suppliers
$150.00/100mg

References

27048-04-0 Synthesis