2-Nitroaniline → Benzofuroxan

Participants

Reaction Steps

18.4 kg (133 moles) of 2-nitroaniline and 0.42 kg (1.3 moles) of tetrabutylammonium bromide are dissolved in 70 kg of toluene. After the addition of 25.3 kg (226 moles) of 50% aqueous potassium hydroxide solution, there is added at 15° to 20° C., during one hour, 110 kg (185 moles) of an aqueous sodium hypochlorite solution. After the addition has been completed, the reaction mixture is allowed to react at 15° to 20° C. for 3 hours, and the aqueous phase is then separated. There is obtained in this manner a solution of benzofurazan-1-oxide in toluene, which solution is suitable for use directly for further reactions, for example for reaction with an acetoacetic acid derivative to the corresponding quinoxaline-1,4-dioxide.

Provenance & Evidence