2-Chloroethanol → 2-((4-Amino-2-chloro-5-nitrophenyl)amino)ethanol

Participants

Reaction Steps

18.7 g (0.1 mole) of 1,4-diamino-2-nitro-5-chlorobenzene were dissolved in 20 ml methylglycol and 12 g ethylenechlorohydrin (1.5 mole) and the solution then heated on a bath having a temperature of 120°C. 6.6 g of sodium hydroxide dissolved in 60 ml water were then slowly added dropwise over a period of 3 hours. Heating was then continued for 1 hour whereupon a chromatographic check wss made to ascertain whether most or all of the starting compound had been reacted. After cooling the mass was diluted with water and the precipitated hydroxyethylated compound was removed by suction. Recrystallation was effected from water and thereafter from a 20% acetic acid. Yield: 4.5 g; m.p.: 130°-131°C. Analysis: C8H10ClO3N3

Provenance & Evidence