N-methyl-2-phenylaniline

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

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

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

Procedure: A solution of 18 g (0.075 mol) of 2-ethoxycarbonylaminobiphenyl in 100 ml of THF is added dropwise to a suspension of 14.2 g (0.373 mol) of lithium aluminum hydride in 300 ml of THF. The mixture is stirred for another 1 hour and then refluxed for 3 hours. Subsequently, while cooling in ice, 28 ml of water are firstly added dropwise and 18 ml of 15% strength aqueous sodium hydroxide are then added. After the precipitate has been separated off, it is washed a number of times with ether. The combined filtrates are dried over sodium sulfate, and the reddish liquid obtained after evaporation of the solvent is fractionated at 0.01 mbar. Bp.: 65-67° C. Yield: 10.64 g=77%. refluxed for 3 hours Subsequently, while cooling in ice After the precipitate has been separated off it is washed a number of times with ether The combined filtrates are dried over sodium sulfate the reddish liquid obtained after evaporation of the solvent

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

Procedure: A solution of 18 g (0.075 mol) of 2-ethoxycarbonylaminobiphenyl in 100 ml of THF is added dropwise to a suspension of 14.2 g (0.373 mol) of lithium aluminum hydride in 300 ml of THF. The mixture is stirred for another 1 hour and then refluxed for 3 hours. Subsequently, while cooling in ice, 28 ml of water are firstly added dropwise and 18 ml of 15% strength aqueous sodium hydroxide are then added. After the precipitate has been separated off, it is washed a number of times with ether. The combined filtrates are dried over sodium sulfate, and the reddish liquid obtained after evaporation of the solvent is fractionated at 0.01 mbar. Bp.: 65-67° C. Yield: 10.64 g=77%. refluxed for 3 hours Subsequently, while cooling in ice After the precipitate has been separated off it is washed a number of times with ether The combined filtrates are dried over sodium sulfate the reddish liquid obtained after evaporation of the solvent

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

Procedure: The starting material is 2-phcnylaniline, which is methylated with potassium carbonate and methyl iodide to obtain N-methyl-2-phenylaniline. The N-methyl-2-phenylaniline is treated with diketene and acid and is cyclized in acetic acid/sulfuric acid as in Example 3 to generate the desired quinolone.

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

Procedure: To a solution of 272 mg (1.0 mmol) 3,5-bis-(trifluoromethyl)phenylacetic acid in 1 ml tetrahydrofuran 162 mg (1.0 mmol) 1,1′-carbonyldiimidazole was added in one portion at 0°. The reaction mixture was stirred for 2 hrs at room temperature and 147 mg (0.8 mmol) biphenyl-2-yl-methyl-amine was added. Stirring was continued for 3 days at room temperature. The reaction mixture was evaporated and the residue was purified by chromatography (SiO2, hexane/ethyl acetate 3:1) to give 160 mg (46%) N-biphenyl-2-yl-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-acetamide as white crystals, MS (ISP): 438.2 (M+H)+. EXAMPLE 15 Stirring was continued for 3 days at room temperature The reaction mixture was evaporated the residue was purified by chromatography (SiO2, hexane/ethyl acetate 3:1)

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

Procedure: A solution of 18 g (0.075 mol) of 2-ethoxycarbonylaminobiphenyl in 100 ml of THF is added dropwise to a suspension of 14.2 g (0.373 mol) of lithium aluminum hydride in 300 ml of THF. The mixture is stirred for another 1 hour and then refluxed for 3 hours. Subsequently, while cooling in ice, 28 ml of water are firstly added dropwise and 18 ml of 15% strength aqueous sodium hydroxide are then added. After the precipitate has been separated off, it is washed a number of times with ether. The combined filtrates are dried over sodium sulfate, and the reddish liquid obtained after evaporation of the solvent is fractionated at 0.01 mbar. Bp.: 65–67° C. Yield: 10.64 g=77%. refluxed for 3 hours Subsequently, while cooling in ice After the precipitate has been separated off it is washed a number of times with ether The combined filtrates are dried over sodium sulfate the reddish liquid obtained after evaporation of the solvent

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

Procedure: To a solution of 272 mg (1.0 mmol) 3,5-bis(trifluoromethyl)phenylacetic acid in 1 ml tetrahydrofuran 162 mg (1.0 mmol) 1,1′-carbonyldiimidazole was added in one portion at 0°. The reaction mixture was stirred for 2 hrs at room temperature and 147 mg (0.8 mmol) biphenyl-2-yl-methyl-amine was added. Stirring was continued for 3 days at room temperature. The reaction mixture was evaporated and the residue was purified by chromatography (SiO2, hexane/ethyl acetate 3:1) to give 160 mg (46%) N-biphenyl-2-yl-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-acetamide as white crystals, MS (ISP): 438.2 (M+H)+. Stirring was continued for 3 days at room temperature The reaction mixture was evaporated the residue was purified by chromatography (SiO2, hexane/ethyl acetate 3:1)

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