2,4-dimethylbenzene-1,3-diamine

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.73 g of para-fluoronitrobenzene (2 eq.) were dissolved in 5 ml of DMSO. 1.2 equivalents of m-xylenediamine and 4 equivalents of triethylamine were added to the solution. The reaction mixture was heated at 60° C. for 20 hours. The mixture was then poured onto crushed ice and a precipitate formed. The latter was filtered, washed with water, and then dried. The mixture was then poured onto crushed ice a precipitate formed The latter was filtered washed with water dried

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.4 g of 2,4-diamino-m-xylene, 9.6 g of 2-chloro-3nitropyridine and 3.0 g of calcium carbonate were introduced into 300 ml water and the resulting mixture was heated under reflux for 8 hours to the boiling temperature. The reaction mixture was filtered while hot, the reaction product precipitating from the filtrate on cooling to 20° C. It was isolated and recrystallized from toluene. 6.2 g of the product melting at 173° to 175° C. were obtained. the resulting mixture was heated under reflux for 8 hours to the boiling temperature The reaction mixture was filtered while hot, the reaction product precipitating from the filtrate It was isolated recrystallized from toluene

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.4 g of 2,4-diamino-m-xylene, 9.6 g of 2-chloro-3nitropyridine and 3.0 g of calcium carbonate were introduced into 300 ml water and the resulting mixture was heated under reflux for 8 hours to the boiling temperature. The reaction mixture was filtered while hot, the reaction product precipitating from the filtrate on cooling to 20° C. It was isolated and recrystallized from toluene. 6.2 g of the product melting at 173° to 175° C. were obtained. the resulting mixture was heated under reflux for 8 hours to the boiling temperature The reaction mixture was filtered while hot, the reaction product precipitating from the filtrate It was isolated recrystallized from toluene

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.76 g of dicobalt octacarbonyl, 1 g of isophthalonitrile and 20 ml of m-xylene were charged into a 100 ml eggplant type flask equipped with a reflux condenser and a gas inlet tube and the air in the flask was thoroughly replaced while introducing carbon monoxide through the gas inlet tube. Thereafter, the flask was heated in an oil bath at 160° C. for 90 minutes under reflux while passing carbon monoxide therethrough. After the heating, the flask was cooled to room temperature and the resulting precipitate was directly transferred into a 100 ml shaking type autoclave together with solvent m-xylene. After adding 9 g of isophthalonitrile and 10 ml of m-xylene thereto, the gas in the autoclave was replaced with hydrogen. Further 10 ml of liquid ammonia was added thereto and the isophthalonitrile was hydrogenated at a reaction temperature of 100° C. under an initially charged hydrogen pressure of 260 kg/cm2 gage. The reaction was completed in 120 minutes and m-xylenediamine was obtained in a yield of 96.4%. equipped with a reflux condenser and a gas inlet tube under reflux After the heating, the flask was cooled to room temperature was hydrogenated at a reaction temperature of 100° C. under an initially charged hydrogen

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

Procedure: 0.76 g of dicobalt octacarbonyl, 0.3 g of various aromatic nitriles and 20 ml of m-xylene as a solvent were charged into a 100 ml eggplant type flask equipped with a reflux condenser and a gas inlet tube, and the air was thoroughly replaced while introducing nitrogen through the gas inlet tube. Thereafter, the flask was heated in an oil bath and the temperature of oil bath was elevated to 160° C. The flask was heated for 90 minutes under reflux conditions while passing nitrogen therethrough, and then the heating was discontinued and the flask was cooled to room temperature. The precipitate formed was directly transferred into a shaking type autoclave having a net capacity of 100 ml together with solvent m-xylene. After adding 10 g of isophthalonitrile and 10 ml of m-xylene thereto, the gas in the autoclave was replaced with nitrogen. After adding 10 ml of liquid ammonia thereto, hydrogen was fed up to a pressure of 260 kg/cm2 gage and the hydrogenation of isophthalonitrile was carried out at a reaction temperature of 100° C. until no absorption of hydrogen took place. The m-xylenediamine thus formed was analyzed by gas chromatography, the results as shown in Table 1 were obtained. equipped with a reflux condenser and a gas inlet tube while introducing nitrogen through the gas inlet tube Thereafter, the flask was heated in an oil bath the temperature of oil bath was elevated to 160° C The flask was heated for 90 minutes under reflux conditions The precipitate formed the hydrogenation of isophthalonitrile was carried out at a reaction temperature of 100° C. until no absorption of hydrogen

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.73 g of para-fluoronitrobenzene (2 eq.) were dissolved in 5 ml of DMSO. 1.2 equivalents of m-xylenediamine and 4 equivalents of triethylamine were added to the solution. The reaction mixture was heated at 60° C. for 20 hours. The mixture was then poured onto crushed ice and a precipitate formed. The latter was filtered, washed with water, and then dried. The mixture was then poured onto crushed ice a precipitate formed The latter was filtered washed with water dried

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.76 g of dicobalt octacarbonyl, 1 g of isophthalonitrile and 20 ml of m-xylene were charged into a 100 ml eggplant type flask equipped with a reflux condenser and a gas inlet tube and the air in the flask was thoroughly replaced while introducing carbon monoxide through the gas inlet tube. Thereafter, the flask was heated in an oil bath at 160° C. for 90 minutes under reflux while passing carbon monoxide therethrough. After the heating, the flask was cooled to room temperature and the resulting precipitate was directly transferred into a 100 ml shaking type autoclave together with solvent m-xylene. After adding 9 g of isophthalonitrile and 10 ml of m-xylene thereto, the gas in the autoclave was replaced with hydrogen. Further 10 ml of liquid ammonia was added thereto and the isophthalonitrile was hydrogenated at a reaction temperature of 100° C. under an initially charged hydrogen pressure of 260 kg/cm2 gage. The reaction was completed in 120 minutes and m-xylenediamine was obtained in a yield of 96.4%. equipped with a reflux condenser and a gas inlet tube under reflux After the heating, the flask was cooled to room temperature was hydrogenated at a reaction temperature of 100° C. under an initially charged hydrogen

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

Procedure: 0.76 g of dicobalt octacarbonyl, 0.3 g of various aromatic nitriles and 20 ml of m-xylene as a solvent were charged into a 100 ml eggplant type flask equipped with a reflux condenser and a gas inlet tube, and the air was thoroughly replaced while introducing nitrogen through the gas inlet tube. Thereafter, the flask was heated in an oil bath and the temperature of oil bath was elevated to 160° C. The flask was heated for 90 minutes under reflux conditions while passing nitrogen therethrough, and then the heating was discontinued and the flask was cooled to room temperature. The precipitate formed was directly transferred into a shaking type autoclave having a net capacity of 100 ml together with solvent m-xylene. After adding 10 g of isophthalonitrile and 10 ml of m-xylene thereto, the gas in the autoclave was replaced with nitrogen. After adding 10 ml of liquid ammonia thereto, hydrogen was fed up to a pressure of 260 kg/cm2 gage and the hydrogenation of isophthalonitrile was carried out at a reaction temperature of 100° C. until no absorption of hydrogen took place. The m-xylenediamine thus formed was analyzed by gas chromatography, the results as shown in Table 1 were obtained. equipped with a reflux condenser and a gas inlet tube while introducing nitrogen through the gas inlet tube Thereafter, the flask was heated in an oil bath the temperature of oil bath was elevated to 160° C The flask was heated for 90 minutes under reflux conditions The precipitate formed the hydrogenation of isophthalonitrile was carried out at a reaction temperature of 100° C. until no absorption of hydrogen

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.73 g of para-fluoronitrobenzene (2 eq.) were dissolved in 5 ml of DMSO. 1.2 equivalents of m-xylenediamine and 4 equivalents of triethylamine were added to the solution. The reaction mixture was heated at 60° C. for 20 hours. The mixture was then poured onto crushed ice and a precipitate formed. The latter was filtered, washed with water, and then dried. The mixture was then poured onto crushed ice a precipitate formed The latter was filtered washed with water dried

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.4 g of 2,4-diamino-m-xylene, 9.6 g of 2-chloro-3nitropyridine and 3.0 g of calcium carbonate were introduced into 300 ml water and the resulting mixture was heated under reflux for 8 hours to the boiling temperature. The reaction mixture was filtered while hot, the reaction product precipitating from the filtrate on cooling to 20° C. It was isolated and recrystallized from toluene. 6.2 g of the product melting at 173° to 175° C. were obtained. the resulting mixture was heated under reflux for 8 hours to the boiling temperature The reaction mixture was filtered while hot, the reaction product precipitating from the filtrate It was isolated recrystallized from toluene

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.76 g of dicobalt octacarbonyl, 1 g of isophthalonitrile and 20 ml of m-xylene were charged into a 100 ml eggplant type flask equipped with a reflux condenser and a gas inlet tube and the air in the flask was thoroughly replaced while introducing carbon monoxide through the gas inlet tube. Thereafter, the flask was heated in an oil bath at 160° C. for 90 minutes under reflux while passing carbon monoxide therethrough. After the heating, the flask was cooled to room temperature and the resulting precipitate was directly transferred into a 100 ml shaking type autoclave together with solvent m-xylene. After adding 9 g of isophthalonitrile and 10 ml of m-xylene thereto, the gas in the autoclave was replaced with hydrogen. Further 10 ml of liquid ammonia was added thereto and the isophthalonitrile was hydrogenated at a reaction temperature of 100° C. under an initially charged hydrogen pressure of 260 kg/cm2 gage. The reaction was completed in 120 minutes and m-xylenediamine was obtained in a yield of 96.4%. equipped with a reflux condenser and a gas inlet tube under reflux After the heating, the flask was cooled to room temperature was hydrogenated at a reaction temperature of 100° C. under an initially charged hydrogen

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

Procedure: 0.76 g of dicobalt octacarbonyl, 0.3 g of various aromatic nitriles and 20 ml of m-xylene as a solvent were charged into a 100 ml eggplant type flask equipped with a reflux condenser and a gas inlet tube, and the air was thoroughly replaced while introducing nitrogen through the gas inlet tube. Thereafter, the flask was heated in an oil bath and the temperature of oil bath was elevated to 160° C. The flask was heated for 90 minutes under reflux conditions while passing nitrogen therethrough, and then the heating was discontinued and the flask was cooled to room temperature. The precipitate formed was directly transferred into a shaking type autoclave having a net capacity of 100 ml together with solvent m-xylene. After adding 10 g of isophthalonitrile and 10 ml of m-xylene thereto, the gas in the autoclave was replaced with nitrogen. After adding 10 ml of liquid ammonia thereto, hydrogen was fed up to a pressure of 260 kg/cm2 gage and the hydrogenation of isophthalonitrile was carried out at a reaction temperature of 100° C. until no absorption of hydrogen took place. The m-xylenediamine thus formed was analyzed by gas chromatography, the results as shown in Table 1 were obtained. equipped with a reflux condenser and a gas inlet tube while introducing nitrogen through the gas inlet tube Thereafter, the flask was heated in an oil bath the temperature of oil bath was elevated to 160° C The flask was heated for 90 minutes under reflux conditions The precipitate formed the hydrogenation of isophthalonitrile was carried out at a reaction temperature of 100° C. until no absorption of hydrogen