ChemicalBook CAS DataBase List 4,6-DICHLORO-PYRIDIN-3-YLAMINE

4,6-DICHLORO-PYRIDIN-3-YLAMINE synthesis

8synthesis methods

Product Name:4,6-DICHLORO-PYRIDIN-3-YLAMINE
CAS Number:7321-93-9
Molecular formula:C5H4Cl2N2
Molecular Weight:163

70593-57-6 Synthesis

70593-57-6
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7321-93-9
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$20.00/100mg

Yield:7321-93-9 73%

Reaction Conditions:

with sodium hydroxide;water;bromine in 1,4-dioxane at 0 - 25; for 18 h;

Steps:

1 Synthesis of 2,4-dichloro-5-nitro-pyridine

NaOH (6.60 g, 165 mmol) was dissolved in H₂O (31 mL) and cooled in an ice bath. Bromine (2.08 mL, 40.6 mmol) was added dropwise and the yellow solution was stirred for 15 min. 4,6-Dichloro-nicotinamide (7.27 g, 38.1 mmol) in 1,4-dioxane (21 mL) was added dropwise to the bromine solution over 30 min. The reaction was allowed to warm slowly to 25° C. over 18 h. The volatiles were removed in vacuo and the resultant solution was diluted with brine and poured into EtOAc. The aqueous phase was separated and extracted twice with EtOAc. The organic layers were combined, dried (Na₂SO₄), decanted and concentrated to afford an orange oil. The resultant oil was purified on a 100 g SiO₂ flash chromatography cartridge with 25 % EtOAc-hexanes to afford 4,6-dichloro-pyridin-3-ylamine as a tan solid (4.54 g, 73%). 30% Aqueous H₂O₂ solution (29 mL) was cooled in an ice bath.

References:

US2006/217417,2006,A1 Location in patent:Page/Page column 13