2-(methoxymethyl)benzene-1,4-diamine

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Into a Parr hydrogenation bottle previously purged with argon, are placed a solution of 2-methoxymethyl-4-nitroaniline (5.0 g, 27.5 mmol) in ethyl acetate (50 mL) and 0.25 g of 10% palladium on carbon. The bottle is mounted on a Parr shaker and hydrogenation is carried out under 50-60 psig (64.7-74.7 psi or 446-515 kPa) of hydrogen pressure. The pressure is carefully monitored for hydrogen uptake and additional hydrogen is introduced to keep the pressure above 50 psig. The hydrogenation is carried out for 3.5 hours after which the catalyst is removed by vacuum filtration. The filtrate is concentrated to about 25 mL and toluene (25 mL) is added to precipitate the product, which is collected by vacuum filtration and dried at 60° C. under vacuum. The product yield is 4.5 g; 1H-NMR (500 MHz, DMSO-d6) δ 3.23 (s, 3 H), 4.11 (s, 2 H), 4.21 (s, 2 H), 4.24 (s, 2 H), 6.33 (dd, 1 H), 6.37 (d, 1 H), 6.41 (d, 1 H). Into a Parr hydrogenation bottle previously purged with argon is introduced after which the catalyst is removed by vacuum filtration The filtrate is concentrated to about 25 mL and toluene (25 mL) is added to precipitate the product, which is collected by vacuum filtration dried at 60° C. under vacuum

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

Procedure: Into a Parr hydrogenation bottle previously purged with argon, are placed a solution of 2-methoxymethyl-4-nitroaniline (5.0 g, 27.5 mmol) in ethyl acetate (50 mL) and 0.25 g of 10% palladium on carbon. The bottle is mounted on a Parr shaker and hydrogenation is carried out under 50-60 psig (64.7-74.7 psi or 446-515 kPa) of hydrogen pressure. The pressure is carefully monitored for hydrogen uptake and additional hydrogen is introduced to keep the pressure above 50 psig. The hydrogenation is carried out for 3.5 hours after which the catalyst is removed by vacuum filtration. The filtrate is concentrated to about 25 mL and toluene (25 mL) is added to precipitate the product, which is collected by vacuum filtration and dried at 60° C. under vacuum. The product yield is 4.5 g; 1H-NMR (500 MHz, DMSO-d6) δ 3.23 (s, 3 H), 4.11 (s, 2 H), 4.21 (s, 2 H), 4.24 (s, 2 H), 6.33 (dd, 1 H), 6.37 (d, 1 H), 6.41 (d, 1 H). Into a Parr hydrogenation bottle previously purged with argon is introduced after which the catalyst is removed by vacuum filtration The filtrate is concentrated to about 25 mL and toluene (25 mL) is added to precipitate the product, which is collected by vacuum filtration dried at 60° C. under vacuum

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

Procedure: 5 g (27.5 mmol) of 4-Nitro-2-methoxymethyl-aminobenzene and 0.250 g of palladium (10% on carbon) are placed in a 250 ml Parr bottle and 50 g of ethyl acetate is added. Hydrogenation is carried out using a Parr apparatus under 50-60 psig (64.7-74.7 psi or 446-515 kPa) of hydrogen pressure. In the course of the reaction the yellowish grey suspension turns to a darker grey suspension. The reaction is also carefully monitored for rapid hydrogen uptake and additional hydrogen is introduced to keep pressure above 50 psig (64.7 psi or 446 kPa). After 1 hour the suspension clears, leaving a yellow solution. The reaction is continued for 2.5 hours to ensure complete conversion. The catalyst is removed by filtration through glass microfiber filter paper. The filtrate is concentrated to ca. 25 ml, and 25 ml of toluene are added to precipitate the product. The product is collected on filter paper with suction and dried at 60° C. under vacuum. The product yield is 4.5 g. is added In the course of the reaction the yellowish grey suspension is introduced leaving a yellow solution The reaction is continued for 2.5 hours The catalyst is removed by filtration through glass microfiber filter paper The filtrate is concentrated to ca. 25 ml, and 25 ml of toluene are added to precipitate the product The product is collected on filter paper with suction dried at 60° C. under vacuum

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

Procedure: Another embodiment of the present application relates to a method of making 2-methoxymethyl-1,4-benzenediamine comprising the steps: (a) introducing ammonia to a 4-nitro-3-methoxymethyl-chlorobenzene to obtain 4-nitro-3-methoxymethyl-aminobenzene; and (b) hydrogenating the 4-nitro-3-methoxymethyl-aminobenzene in the presence of a hydrogenation catalyst to obtain the 2-methoxymethyl-1,4-benzenediamine.

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

Procedure: 5 g (27.5 mmol) of 4-Nitro-2-methoxymethyl-aminobenzene and 0.250 g of palladium (10% on carbon) are placed in a 250 ml Parr bottle and 50 g of ethyl acetate is added. Hydrogenation is carried out using a Parr apparatus under 50-60 psig (64.7-74.7 psi or 446-515 kPa) of hydrogen pressure. In the course of the reaction the yellowish grey suspension turns to a darker grey suspension. The reaction is also carefully monitored for rapid hydrogen uptake and additional hydrogen is introduced to keep pressure above 50 psig (64.7 psi or 446 kPa). After 1 hour the suspension clears, leaving a yellow solution. The reaction is continued for 2.5 hours to ensure complete conversion. The catalyst is removed by filtration through glass microfiber filter paper. The filtrate is concentrated to ca. 25 ml, and 25 ml of toluene are added to precipitate the product. The product is collected on filter paper with suction and dried at 60° C. under vacuum. The product yield is 4.5 g. is added In the course of the reaction the yellowish grey suspension is introduced leaving a yellow solution The reaction is continued for 2.5 hours The catalyst is removed by filtration through glass microfiber filter paper The filtrate is concentrated to ca. 25 ml, and 25 ml of toluene are added to precipitate the product The product is collected on filter paper with suction dried at 60° C. under vacuum

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

Procedure: Another embodiment of the present application relates to a method of making 2-methoxymethyl-1,4-benzenediamine comprising the steps: (a) introducing ammonia to a 4-nitro-3-methoxymethyl-chlorobenzene to obtain 4-nitro-3-methoxymethyl-aminobenzene; and (b) hydrogenating the 4-nitro-3-methoxymethyl-aminobenzene in the presence of a hydrogenation catalyst to obtain the 2-methoxymethyl-1,4-benzenediamine.

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

Procedure: Into a Parr hydrogenation bottle previously purged with argon, are placed a solution of 2-methoxymethyl-4-nitroaniline (5.0 g, 27.5 mmol) in ethyl acetate (50 mL) and 0.25 g of 10% palladium on carbon. The bottle is mounted on a Parr shaker and hydrogenation is carried out under 50-60 psig (64.7-74.7 psi or 446-515 kPa) of hydrogen pressure. The pressure is carefully monitored for hydrogen uptake and additional hydrogen is introduced to keep the pressure above 50 psig. The hydrogenation is carried out for 3.5 hours after which the catalyst is removed by vacuum filtration. The filtrate is concentrated to about 25 mL and toluene (25 mL) is added to precipitate the product, which is collected by vacuum filtration and dried at 60° C. under vacuum. The product yield is 4.5 g. 1H-NMR (500 MHz, DMSO-d6) δ 3.23 (s, 3H), 4.11 (s, 2H), 4.21 (s, 2H), 4.24 (s, 2H), 6.33 (dd, 1H), 6.37 (d, 1H), 6.41 (d, 1H). Into a Parr hydrogenation bottle previously purged with argon is introduced after which the catalyst is removed by vacuum filtration The filtrate is concentrated to about 25 mL and toluene (25 mL) is added to precipitate the product, which is collected by vacuum filtration dried at 60° C. under vacuum

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

Procedure: Into a Parr hydrogenation bottle previously purged with argon, are placed a solution of 2-methoxymethyl-4-nitroaniline (5.0 g, 27.5 mmol) in ethyl acetate (50 mL) and 0.25 g of 10% palladium on carbon. The bottle is mounted on a Parr shaker and hydrogenation is carried out under 50-60 psig (64.7-74.7 psi or 446-515 kPa) of hydrogen pressure. The pressure is carefully monitored for hydrogen uptake and additional hydrogen is introduced to keep the pressure above 50 psig. The hydrogenation is carried out for 3.5 hours after which the catalyst is removed by vacuum filtration. The filtrate is concentrated to about 25 mL and toluene (25 mL) is added to precipitate the product, which is collected by vacuum filtration and dried at 60° C. under vacuum. The product yield is 4.5 g; 1H-NMR (500 MHz, DMSO-d6) δ 3.23 (s, 3 H), 4.11 (s, 2 H), 4.21 (s, 2 H), 4.24 (s, 2 H), 6.33 (dd, 1 H), 6.37 (d, 1 H), 6.41 (d, 1 H). Into a Parr hydrogenation bottle previously purged with argon is introduced after which the catalyst is removed by vacuum filtration The filtrate is concentrated to about 25 mL and toluene (25 mL) is added to precipitate the product, which is collected by vacuum filtration dried at 60° C. under vacuum