benzene-1,4-diamine;dihydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.75 mole (10.5 g) of 3-amino-4-methoxy phenol is dissolved in 50 cc of acetone to which have been added 50 cc of ammonia (22° Be') and 250 cc of H2O2 (20 volumes). To this solution there is immediately added 0.05 mole (9.0 g) of paraphenylene diamine dihydrochloride in solution in 100 cc of water. The resulting reaction mixture is agitated for two hours at ambient temperature at which time the reaction mixture is filtered to recover the precipitate which has formed. After recrystallizing the precipitate in ethylacetate and washing the recrystallized product initially with a little methyl cellosolve and then with a little ether, 2-amino-5-[4'-(amino)anilino]-1,4-benzoquinone is obtained which is chromatographically pure and which melts with decomposition above 260° C. The resulting reaction mixture is filtered to recover the precipitate which has formed After recrystallizing the precipitate in ethylacetate washing the recrystallized product initially with a little methyl cellosolve

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.75 mole (10.5 g) of 3-amino-4-methoxy phenol is dissolved in 50 cc of acetone to which have been added 50 cc of ammonia (22° Be) and 250 cc of H2O2 (20 volumes). To this solution there is immediately added 0.05 mole (9.0 g) of paraphenylene diamine dihydrochloride in solution in 100 cc of water. The resulting reaction mixture is agitated for two hours at ambient temperature at which time the reaction mixture is filtered to recover the precipitate which has formed. After recrystallizing the precipitate in ethylacetate and washing the recrystallized product initially with a little methyl cellosolve and then with a little ether, 2-amino-5-[4'-(amino)anilino]-1,4-benzoquinone is obtained which is chromatographically pure and which melts with decomposition above 260° C. The resulting reaction mixture is filtered to recover the precipitate which has formed After recrystallizing the precipitate in ethylacetate washing the recrystallized product initially with a little methyl cellosolve

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.75 mole (10.5 g) of 3-amino-4-methoxy phenol is dissolved in 50 cc of acetone to which have been added 50 cc of ammonia (22° Be) and 250 cc of H2O2 (20 volumes). To this solution there is immediately added 0.05 mole (9.0 g) of paraphenylene diamine dihydrochloride in solution in 100 cc of water. The resulting reaction mixture is agitated for two hours at ambient temperature at which time the reaction mixture is filtered to recover the precipitate which has formed. After recrystallizing the precipitate in ethylacetate and washing the recrystallized product initially with a little methyl cellosolve and then with little ether, 2-amino-5-[4'-(amino)anilino]-1,4-benzoquinone is obtained which is chromatographically pure and which melts with decomposition above 260° C. The resulting reaction mixture is filtered to recover the precipitate which has formed After recrystallizing the precipitate in ethylacetate washing the recrystallized product initially with a little methyl cellosolve

Conditions: temp:189.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of p-diaminobenzene dihydrochloride (20.1 g, 0.11 mole), 2-oxazolidinone (17.4 g, 0.20 mole) and 100 ml of 2-(2-methoxyethoxy)ethanol was heated to 189° C. in an oil bath while being vigorously stirred mechanically. After two and one-half hours, all gas evolution had ceased and the dark purple reaction mixture was allowed to cool to room temperature. Most of the solvent was removed in vacuo while applying heat (95° C./10 mm Hg) to give a viscous, dark purple oil. After dissolution of the crude triamine dihydrochloride in 100 ml of a 10 percent aqueous sodium hydroxide solution, the free amine was extracted with three portions of chloroform. During the extraction, solid sodium chloride was added to help break up the emulsion which formed. The combined chloroform portions were dried over anhydrous potassium carbonate and filtered. After removal of the solvent in vacuo, approximately 20 g of the crude amine was obtained as a dark yellow oil. Kugelrohr distillation (bulb to bulb) at 160° C. to 190° C. (0.1 mm Hg) afforded a 29 percent yield of the triamine as a pale yellow oil. The product structure was confirmed by spectral studies. to cool to room temperature Most of the solvent was removed in vacuo while applying heat (95° C./10 mm Hg) to give a viscous, dark purple oil the free amine was extracted with three portions of chloroform During the extraction, solid sodium chloride was added formed The combined chloroform portions were dried over anhydrous potassium carbonate filtered After removal of the solvent in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.75 mole (10.5 g) of 3-amino-4-methoxy phenol is dissolved in 50 cc of acetone to which have been added 50 cc of ammonia (22° Be') and 250 cc of H2O2 (20 volumes). To this solution there is immediately added 0.05 mole (9.0 g) of paraphenylene diamine dihydrochloride in solution in 100 cc of water. The resulting reaction mixture is agitated for two hours at ambient temperature at which time the reaction mixture is filtered to recover the precipitate which has formed. After recrystallizing the precipitate in ethylacetate and washing the recrystallized product initially with a little methyl cellosolve and then with a little ether, 2-amino-5-[4'-(amino)anilino]-1,4-benzoquinone is obtained which is chromatographically pure and which melts with decomposition above 260° C. The resulting reaction mixture is filtered to recover the precipitate which has formed After recrystallizing the precipitate in ethylacetate washing the recrystallized product initially with a little methyl cellosolve

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.75 mole (10.5 g) of 3-amino-4-methoxy phenol is dissolved in 50 cc of acetone to which have been added 50 cc of ammonia (22° Be') and 250 cc of H2O2 (20 volumes). To this solution there is immediately added 0.05 mole (9.0 g) of paraphenylene diamine dihydrochloride in solution in 100 cc of water. The resulting reaction mixture is agitated for two hours at ambient temperature at which time the reaction mixture is filtered to recover the precipitate which has formed. After recrystallizing the precipitate in ethylacetate and washing the recrystallized product initially with a little methyl cellosolve and then with a little ether, 2-amino-5-[4'-(amino)anilino]-1,4-benzoquinone is obtained which is chromatographically pure and which melts with decomposition above 260° C. The resulting reaction mixture is filtered to recover the precipitate which has formed After recrystallizing the precipitate in ethylacetate washing the recrystallized product initially with a little methyl cellosolve