Hydrochloric Acid → HCID 21884193, compound

Participants

Reaction Steps

To a solution of N-methyl-3-butylamino-4-nitrobenzamide (380 mg, 1.51 mmol) in anhydrous THF (20 mL) was added a solution of borane-THF (3.78 mL of a 2 M solution, 7.56 mmol) and the solution was stirred at room temperature 30 min, and then was warmed to reflux overnight. The solution was allowed to cool to room temperature, 1 N HCl was added to quench the reaction, and the aqueous was washed with ethyl acetate. The aqueous was made basic with 1 N NaOH and extracted with ethyl acetate. The combined organic extracts were dried over MgSO4 and concentrated to give the product N-butyl-5-methylaminomethyl-2-nitroaniline (275 mg, 77%), approximately 90% pure by NMR and LCMS.

Provenance & Evidence