2-(N-ethyl-m-toluidino)ethanol → 3-methyl-4-(2-methoxy-4-nitrophenylazo)-N-ethyl-N-hydroxyethylaniline

Participants

Reaction Steps

16.8 g (0.1 mol) of 2-methoxy-4-nitroaniline was diazotized in a conventional manner using 7.0 g of sodium nitrite and subjected to coupling with 17.9 g (0.1 mol) of N-ethyl-N-hydroxyethyl-m-toluidine to obtain 34.4 g of 3-methyl-4-(2-methoxy-4-nitrophenylazo)-N-ethyl-N-hydroxyethylaniline. 17.9 g (0.05 mol) of the compound thus obtained was added to 50 ml of pyridine and then to the mixture was added little by little 29 g of p-toluenesulfonyl chloride at a temperature range between 10° C. and 15° C. After the completion of the addition, the mixture was stirred at room temperature for 2 hours, then the reaction solution was poured into cool diluted hydrochloric acid and the resulting red colored precipitate was collected by filtration. The crude product was recrystallized from diluted acetone to obtain 14.2 g of 3-methyl-4-(2-methoxy-4-nitrophenylazo)-N-ethyl-N-toluenesulfonyloxyethylaniline [5-b].

Provenance & Evidence