Dimethylamine → HCID 21473553, compound

Participants

Reaction Steps

A mixture of 5-methyl-2-nitrobenzoic acid (10 g, 55.2 mmol) and oxalyl chloride (6 mL, 68.8 mmol) in 100 mL of methylene chloride was stirred under argon at room temperature for 2 hours. The mixture was concentrated and the residue was co-evaporated twice with toluene. The residue was dissolved in 60 mL of dioxane and the solution was added dropwise to a mixture of aqueous dimethylamine (8.2 g, 40% w/w, 72.7 mmol) and sodium hydroxide (2.2 g, 55 mmol) in 20 mL of dioxane at 0° C. The mixture was stirred at room temperature for 1 hour and then poured into water. The mixture was extracted with ethyl acetate (2×150 mL), dried (Na2SO4), filtered and concentrated to give N,N,5-trimethyl-2-nitrobenzamide (11 g, 52.8 mmol).

Provenance & Evidence