4-decylaniline

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

Procedure: In a 500-ml round-bottom flask is placed 2.03 g (0.005 mole) of 2,4,6-triphenylpyrylium bisulfate. To this is added 150 ml of ethanol followed by 2.34 g (0.01 mole) of p-decylaniline. This mixture is refluxed for about 8 hours and allowed to cool. A quantity of the starting aniline precipitates and is removed by filtration. The ethanol is then removed to give a yellow waxy material which is washed with ether to give a white powder. This material is then dissolved in acetonitrile to cause the remaining aniline to precipitate. The acetonitrile is removed to give the desired product which is then rinsed with ether to remove any residual acetonitrile. The yield is 1.77 g (0.0028 mole) of 2,4,6-triphenylpyridinium bisulfate as confirmed by nuclear magnetic resonance (1H) and elemental analysis. In a 500-ml round-bottom flask is placed This mixture is refluxed for about 8 hours to cool A quantity of the starting aniline precipitates is removed by filtration The ethanol is then removed to give a yellow waxy material which is washed with ether to give a white powder to precipitate The acetonitrile is removed

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

Procedure: A mixture of 4-(1-decenyl)nitrobenzene (12.2 g), acetic acid (120 ml) and palladium black (0.84 g) was hydrogenated at room temperature and at 3-4 atm for 12 hours. The catalyst was changed and the reaction was continued under the same conditions for 12 hours. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give 10.9 g of 4-decylaniline. the reaction was continued under the same conditions for 12 hours The catalyst was filtered off the filtrate was concentrated under reduced pressure

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

Procedure: In a 500-ml round-bottom flask is placed 2.03 g (0.005 mole) of 2,4,6-triphenylpyrylium bisulfate. To this is added 150 ml of ethanol followed by 2.34 g (0.01 mole) of p-decylaniline. This mixture is refluxed for about 8 hours and allowed to cool. A quantity of the starting aniline precipitates and is removed by filtration. The ethanol is then removed to give a yellow waxy material which is washed with ether to give a white powder. This material is then dissolved in acetonitrile to cause the remaining aniline to precipitate. The acetonitrile is removed to give the desired product which is then rinsed with ether to remove any residual acetonitrile. The yield is 1.77 g (0.0028 mole) of 2,4,6-triphenylpyridinium bisulfate as confirmed by nuclear magnetic resonance (1H) and elemental analysis. In a 500-ml round-bottom flask is placed This mixture is refluxed for about 8 hours to cool A quantity of the starting aniline precipitates is removed by filtration The ethanol is then removed to give a yellow waxy material which is washed with ether to give a white powder to precipitate The acetonitrile is removed

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

Procedure: In a 500-ml round-bottom flask is placed 2.03 g (0.005 mole) of 2,4,6-triphenylpyrylium bisulfate. To this is added 150 ml of ethanol followed by 2.34 g (0.01 mole) of p-decylaniline. This mixture is refluxed for about 8 hours and allowed to cool. A quantity of the starting aniline precipitates and is removed by filtration. The ethanol is then removed to give a yellow waxy material which is washed with ether to give a white powder. This material is then dissolved in acetonitrile to cause the remaining aniline to precipitate. The acetonitrile is removed to give the desired product which is then rinsed with ether to remove any residual acetonitrile. The yield is 1.77 g (0.0028 mole) of 2,4,6-triphenylpyridinium bisulfate as confirmed by nuclear magnetic resonance (1H) and elemental analysis. In a 500-ml round-bottom flask is placed This mixture is refluxed for about 8 hours to cool A quantity of the starting aniline precipitates is removed by filtration The ethanol is then removed to give a yellow waxy material which is washed with ether to give a white powder to precipitate The acetonitrile is removed

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

Procedure: A mixture of 4-(1-decenyl)nitrobenzene (12.2 g), acetic acid (120 ml) and palladium black (0.84 g) was hydrogenated at room temperature and at 3-4 atm for 12 hours. The catalyst was changed and the reaction was continued under the same conditions for 12 hours. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give 10.9 g of 4-decylaniline. the reaction was continued under the same conditions for 12 hours The catalyst was filtered off the filtrate was concentrated under reduced pressure

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

Procedure: To a tetrahydrofuran (20 ml) solution of 4-decylaniline (3.07 g, 13.14 mmol), cooled to 0°-5° C. (inert atmosphere), is added n-butyllithium (2.3 M, 13.14 mmol). The deeply colored solution is stirred for ten minutes, after which a tetrahydrofuran (20 ml) solution of methyl 3-phenylsalicylate (1.00 g, 4.38 mmol) is added. The temperature is allowed to rise to 25° C. over a 30 minute period. The reaction is quenched by pouring the contents into 10% hydrochloric acid (100 ml). The organics are extracted into ethyl acetate, washed with 10% hydrochloric acid, dried (sodium sulfate), and concentrated to give 2.77 g of crude solid. Chromatography (Kieselgel 60, dichloromethane) affords N-(4-decylphenyl)-2-hydroxy-[1,1'-biphenyl]-3-carboxamide (1.69 g, 90%), mp 74°-75° C. The reaction is quenched by pouring the contents into 10% hydrochloric acid (100 ml) The organics are extracted into ethyl acetate washed with 10% hydrochloric acid dried (sodium sulfate) concentrated to give 2.77 g of crude solid

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

Procedure: A mixture of 4-(1-decenyl)nitrobenzene (12.2 g), acetic acid (120 ml) and palladium black (0.84 g) was hydrogenated at room temperature and at 3-4 atm for 12 hours. The catalyst was changed and the reaction was continued under the same conditions for 12 hours. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give 10.9 g of 4-decylaniline. the reaction was continued under the same conditions for 12 hours The catalyst was filtered off the filtrate was concentrated under reduced pressure

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

Procedure: In a 500-ml round-bottom flask is placed 2.03 g (0.005 mole) of 2,4,6-triphenylpyrylium bisulfate. To this is added 150 ml of ethanol followed by 2.34 g (0.01 mole) of p-decylaniline. This mixture is refluxed for about 8 hours and allowed to cool. A quantity of the starting aniline precipitates and is removed by filtration. The ethanol is then removed to give a yellow waxy material which is washed with ether to give a white powder. This material is then dissolved in acetonitrile to cause the remaining aniline to precipitate. The acetonitrile is removed to give the desired product which is then rinsed with ether to remove any residual acetonitrile. The yield is 1.77 g (0.0028 mole) of 2,4,6-triphenylpyridinium bisulfate as confirmed by nuclear magnetic resonance (1H) and elemental analysis. In a 500-ml round-bottom flask is placed This mixture is refluxed for about 8 hours to cool A quantity of the starting aniline precipitates is removed by filtration The ethanol is then removed to give a yellow waxy material which is washed with ether to give a white powder to precipitate The acetonitrile is removed

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

Procedure: In a 500-ml round-bottom flask is placed 2.03 g (0.005 mole) of 2,4,6-triphenylpyrylium bisulfate. To this is added 150 ml of ethanol followed by 2.34 g (0.01 mole) of p-decylaniline. This mixture is refluxed for about 8 hours and allowed to cool. A quantity of the starting aniline precipitates and is removed by filtration. The ethanol is then removed to give a yellow waxy material which is washed with ether to give a white powder. This material is then dissolved in acetonitrile to cause the remaining aniline to precipitate. The acetonitrile is removed to give the desired product which is then rinsed with ether to remove any residual acetonitrile. The yield is 1.77 g (0.0028 mole) of 2,4,6-triphenylpyridinium bisulfate as confirmed by nuclear magnetic resonance (1H) and elemental analysis. In a 500-ml round-bottom flask is placed This mixture is refluxed for about 8 hours to cool A quantity of the starting aniline precipitates is removed by filtration The ethanol is then removed to give a yellow waxy material which is washed with ether to give a white powder to precipitate The acetonitrile is removed

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

Procedure: A mixture of 4-(1-decenyl)nitrobenzene (12.2 g), acetic acid (120 ml) and palladium black (0.84 g) was hydrogenated at room temperature and at 3-4 atm for 12 hours. The catalyst was changed and the reaction was continued under the same conditions for 12 hours. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give 10.9 g of 4-decylaniline. the reaction was continued under the same conditions for 12 hours The catalyst was filtered off the filtrate was concentrated under reduced pressure