3,4-Dichloroaniline → Methyl 5-(3,4-dichlorophenylamino)pyrazine-2-carboxylate

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Reaction Conditions

Reaction Steps

A mixture of 3,4-dichloroaniline (1.127 g, 6.95 mmol) and methyl 5-chloropyrazine-2-carboxylate (0.6 g, 3.48 mmol) in dioxane (32 mL) was heated at 100° C. for 7 days, then cooled to room temperature and concentrated. The residue was triturated with methanol and filtered. The brown filter cake was washed with methanol and dried to yield methyl 5-(3,4-dichlorophenylamino)pyrazine-2-carboxylate (0.53 g, 51%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.44 (1H, s), 8.81 (1H, d, J=1.26 Hz), 8.30 (1H, d, J=1.51 Hz), 8.21 (1H, d, J=2.26 Hz), 7.46-7.73 (2H, m), 3.58 (2H, s). LCMS: R.T.=4.07; [M+H]+=298.12.

Provenance & Evidence