2-Methoxyaniline → HCID 24985363, compound

Participants

Reaction Conditions

Reaction Steps

6-Chloro-N-(2-methoxyphenyl)-3-nitropyridin-2-amine. 2,6-Dichloro-3-nitropyridine (3.0 g, 15.54 mmol) was dissolved in tetrahydrofuran (50 mL) and cooled to −78° C. A solution of o-anisidine (1.91 g, 15.54 mmol) and diisopropylamine (2.10 g, 16.31 mmol) in tetrahydrofuran (5 mL) was added dropwise. The mixture was stirred at ambient temperature for 16 h. The solution was condensed under reduced pressure and partitioned between water and ethyl acetate (3×), organics were pooled and dried over magnesium sulfate, filtered and solvent removed under reduced pressure to give the crude product. The solid was triturated with ethyl acetate/hexanes and the resultant precipitate filtered to afford the title compound (3.53 g, 81%). MS (ESI) m/z 280.1 [M+1]+.

Provenance & Evidence