Reaction #674283

Reaction equation

hydrogen peroxide

N-ethyl-N-isopropyl-4-aminoaniline hydrochloride

4-butoxybenzene-1,3-diamine dihydrochloride

ethanol

ammonia

→

2-[[4-(2-amino-5-butoxy-4-iminocyclohexa-2,5-dienylideneamino)phenyl](2-hydroxyethyl)amino]ethanol

Solvents

water

Conditions

Workup

1. 1
   Otherthe ethanol is removed
2. 2
   Otherthe coupling product formed
3. 3
   Extractionis extracted with butanol
4. 4
   OtherAfter removal of the butanol under vacuum

Procedure

To a solution of 0.925 g (0.003 mol) of N-ethyl-N-isopropyl-4-aminoaniline hydrochloride and 0.76 g (0.003 mol) of 4-butoxybenzene-1,3-diamine dihydrochloride in 2 ml of water and 6 ml of ethanol, brought to pH 9.5 with 20% aqueous ammonia, are added 10.2 ml of 6% aqueous hydrogen peroxide solution. After stirring for 24 hours at room temperature, the ethanol is removed and the coupling product formed is extracted with butanol. After removal of the butanol under vacuum, the gummy residue is taken up in ethyl acetate and then in ether. 0.470 g of 2-[[4-(2-amino-5-butoxy-4-iminocyclohexa-2,5-dienylideneamino)phenyl](2-hydroxyethyl)amino]ethanol 10 is obtained in the form of a blue-black powder after drying.

Source