2-(3-methylbutyl)aniline

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

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

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

Procedure: To a mixture composed of 10 ml of methanol, 1.3 g (6.4 mmol) of the above 2-(3-methylbutyl)nitrobenzene, and 6.4 ml of concentrated aqueous hydrochloric acid solution, 1.4 g (25.1 mmol) of reduced iron was added in portions and heated to 60° C. with stirring for 1 hour. The reaction mass was poured into water, neutralized with a saturated aqueous sodium hydrogen carbonate solution and filtered to move precipitated iron hydroxide. The filtrate was extracted with ethyl acetate, washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 0.95 g of the desired product as oil. Yield was 85%. was added in portions filtered to move precipitated iron hydroxide The filtrate was extracted with ethyl acetate washed with a saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure

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

Procedure: To a mixture composed of 10 ml of methanol, 1.3 g (6.4 mmol) of the above 2-(3-methylbutyl)nitrobenzene, and 6.4 ml of concentrated aqueous hydrochloric acid solution, 1.4 g (25.1 mmol) of reduced iron was added in portions and heated to 60° C. with stirring for 1 hour. The reaction mass was poured into water, neutralized with a saturated aqueous sodium hydrogen carbonate solution and filtered to remove precipitated iron hydroxide. The filtrate was extracted with ethyl acetate, washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 0.95 g of the desired product as oil. Yield was 85%. was added in portions filtered to remove precipitated iron hydroxide The filtrate was extracted with ethyl acetate washed with a saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure

Conditions: temp:210.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution comprising 8.0 g (0.045 mol) of 1-(2-aminophenyl)-3-methylbutan-1-one (X-1), 6.8 g (0.135 mol) of hydrazine hydrate and 7.6 g (0.135 mol) of potassium hydroxide in 90 ml of triethylene glycol is heated at 210° C. for 6 h. For work-up, water and ethyl acetate are added at room temperature. The organic phase is again washed with water, dried over magnesium sulphate and concentrated under reduced pressure. Purification by column chromatography (cyclohexane/ethyl acetate 3:1) gives 5.3 g (71.5% of theory) of [2-(3-methylbutyl)-phenyl]amine. The organic phase is again washed with water dried over magnesium sulphate concentrated under reduced pressure Purification by column chromatography (cyclohexane/ethyl acetate 3:1)

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

Procedure: 326.5 mg (2.0 mmol) of [2-(3-methylbutyl)phenyl]amine (III-1) are added to a solution comprising 388.5 mg (2.2 mmol) of 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride and 0.45 ml (3.2 mmol) of triethylamine in 20 ml of tetrahydrofuran. The reaction solution is stirred at 60° C. for 90 min, filtered through silica gel and concentrated. Column chromatography (cyclohexane/ethyl acetate gradient) gives 592 mg (98% of theory) of 5-fluoro-1,3-dimethyl-N-[2-(3-methylbutyl)phenyl]-1H-pyrazole-4-carboxamide of logP (pH 2.3)=3.12. filtered through silica gel concentrated