Hydrochloric Acid → HCID 67021636, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-3-nitro-pyridine (5.0 g, 31.4 mmol), (4-amino-2,6-dichloro-phenyl)-acetic acid methyl ester (7.8 g 33.3 mmol), and a 4 N solution of HCl in dioxane (12 mL, 48.0 mmol, 2.9 equiv) in MeOH/dioxane (60 mL; 1:1, v/v) is stirred for 46.5 h at 100° C. The reaction mixture is allowed to cool to rt and concentrated in vacuo. The residue is dissolved in EtOAc, washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated. Purification of the crude product by silica gel column chromatography (Hexane/EtOAc, 4:1), followed by trituration in diethyl ether, provides the title compound: ES-MS: 355.9/357.9 [M+H]+; tR=5.33 min (System 1); Rf=0.25 (Hexane/EtOAc, 4:1).

Provenance & Evidence