Formaldehyde → N1,6-dimethylbenzene-1,3-diamine

Participants

Reaction Steps

15.4 g. (0.1M) of 2-amino-4-nitrotoluene was dissolved in 100 ml. 96% H2SO4 at room temperature with stirring and 50 ml. of a 36% solution of formaldehyde in H2O was added. The mixture was stirred for 30 minutes and poured on ice, neutralized with NaOH, filtered and washed. There was obtained 16.1 g. of 2-methylamino-4-nitrotoluene; m.p. 107°-108° (Gnehm/Blume. Ann. 304, 100, gives 107.5° C). 8.3 g. of the above compound was reduced catalytically with Pd as catalyst and the free amine produced was reacted with HCl to form 10 g. of the dihydrochloride (the free amine is liquid). ##STR9##

Provenance & Evidence