I want to prepare 2,3-diaminophenazine. i have tried with both the following procedure. But i cant get the white or brown colour precipitate. Could you help me in the synthesis of this compound.?
Synthesis of 2,3-diaminophenazine (Ref: Can. J. Chem. 89: 1202–1206 (2011))
2,3-Diaminophenazine was prepared by using a modified procedure reported in the literature.10 In a typical experiment, 6 mL of 0.08 mol/L aq FeCl3 solution was rapidly added into 30 mL of a 0.02 mol/L aqueous o-phenylenediamine solution with vigorous stirring. A quick color change from purpleblack to reddish-brown was observed upon the addition of FeCl3. After 5 h at ambient temperature, a large amount of white solid was formed. The precipitate was washed three times with deionized water, then separated by centrifugation and sublimated to afford 1 as a white needlelike crystal.
Synthesis of 2,3-diaminophenazine (Ref: Acta Cryst. (2001). C57, 104-105)
2,3-Diaminophenazine was prepared by addition of a stoichiometric quantity of copper(II) hydroxide to an aqueous suspension of 1,2- phenylenediamine. The resultant brown precipitate was collected by ® ltration and subsequently crystallized by slow diffusion of acetonitrile vapour into a methanolic solution of the title compound.
OPD, 5.0 g (0.046 mol), was dissolved in 200 mL of 1.0 M HCl.
To this solution was added 5.0 g (0.022 mol) of ammonium
peroxydisulfate, producing a homogenous solution after stirring.
The reaction mixture was allowed to stand at room temperature
for 48 h. Filtration yielded ∼1 g of black needles. Anal. Calcd
for 30% 1 (C12H10N4‚HCl‚2H2O) + 70% 2 (C12H9N3O‚HCl‚
2H2O): C, 50.85; H, 5.09; N, 16.30; Cl, 12.51. Found: C, 49.45;
H, 4.63; N, 15.50; Cl, 13.54.
Separation of 1 and 2 was completed by dissolving the black
needles in 150 mL of 2 M NaOH, filtering any undissolved solid,and extracting the aqueous solution six times with 50 mL
portions of dichloromethane. The aqueous layer was acidified
to pH ∼7, and the precipitated solid 2 was filtered and washed
with distilled water. A sharp, small shoulder at 6.89 ppm in
the proton spectrum indicates that a minute quantity of 2,3-
diaminophenazine is still present.
Mr. Kumar,
You could try with some of the following conditions:
1) Benzene-1,2-diamine, acetyl chloride in chloroform;
2) Benzene-1,2-diamine, CuCl2·2H2O; sodium methylate in methanol, 24 h;
3) Benzene-1,2-diamine, cyclohexa-2,5-diene-1,4-dione, hydrogenchloride;
4) Benzene-1,2-diamine, cyclohexa-2,5-diene-1,4-dione silver(l) oxide, diethyl ether;
5) Benzene-1,2-diamine and hydrogenchloride; Cu(2+) in ethanol; water, T=25°C;
6) Benzene-1,2-diamin, I2 and C6H6.
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