4-chloro-2-(trifluoromethyl)aniline

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-amino-5-chlorobenzotrifluoride (1.01 g, 5.16 mmol, Aldrich) in acetic anhydride (5 mL) was stirred at room temperature for 12 h to produce white needle precipitate. It was filtered to give 1.123 g (91.7%) of 2-acetamido-5-chlorobenzotrifluoride. 1H NMR (CDCl3): δ2.214 (s, 3H); 7.359 (br, 1H); 7.512 (d, 1H, J=9 Hz), 7.581 (s, 1H); 7.163 (d, 1H, J=8.4 Hz). to produce white needle precipitate It was filtered

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: VPC assay of the organic product revealed the following composition (15% XE 60 column packing; 120° C-250° C; 4°/min.): o-aminobenzotrifluoride (13.1 wt. %; 25.94 grams; 0.161 mole; 83.9% conversion); 2-amino-5-chlorobenzotrifluoride, 53.5 wt. %; 105.9 grams or 64.5% corrected yield); and, 2-amino-3,5-dichlorobenzotrifluoride, 33.3 wt. %; 65.93 grams or 34.2% corrected yield). A trace of 2-amino-3-chlorobenzotrifluoride was produced. 120° C-250° C 105.9 grams or 64.5% corrected yield) 65.93 grams or 34.2% corrected yield)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: VPC assay of the organic product revealed the following composition (15% XE 60 column packing; 120° C-250° C; 4°/min.): o-aminobenzotrifluoride (13.1 wt. %; 25.94 grams; 0.161 mole; 83.9% conversion); 2-amino-5-chlorobenzotrifluoride, 53.5 wt. %; 105.9 grams or 64.5% corrected yield); and, 2-amino-3,5-dichlorobenzotrifluoride, 33.3 wt. %; 65.93 grams or 34.2% corrected yield). A trace of 2-amino-3-chlorobenzotrifluoride was produced. 120° C-250° C 105.9 grams or 64.5% corrected yield) 65.93 grams or 34.2% corrected yield)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a similar manner to Example 133, 4-tert-butoxycarbonylaminobicyclo[2.2.2]octane-1-carboxylic acid (150 mg) and 2-amino-5-chlorobenzotrifluoride (173 μL) were used to obtain 4-tert-butoxycarbonylamino-N-(4-chloro-2-trifluoromethylphenyl)bicyclo[2.2.2]octane-1-carboxamide (79.7 mg).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-amino-5-chlorobenzotrifluoride (1.01 g, 5.16 mmol, Aldrich) in acetic anhydride (5 mL) was stirred at room temperature for 12 h to produce white needle precipitate. It was filtered to give 1.123 g (91.7%) of 2-acetamido-5-chlorobenzotrifluoride. 1H NMR (CDCl3): δ2.214 (s, 3H); 7.359 (br, 1H); 7.512 (d, 1H, J=9 Hz), 7.581 (s, 1H); 7.163 (d, 1H, J=8.4 Hz). to produce white needle precipitate It was filtered

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-amino-5-chlorobenzotrifluoride (1.01 g, 5.16 mmol, Aldrich) in acetic anhydride (5 mL) was stirred at room temperature for 12 h to produce white needle precipitate. It was filtered to give 1.123 g (91.7%) of 2-acetamido-5-chlorobenzotrifluoride. 1H NMR (CDCl3): δ 2.214 (S, 3H); 7.359 (br, 1H); 7.512 (d, 1H, J=9 Hz), 7.581 (s, 1H); 7.163 (d, 1H, J=8.4 Hz). to produce white needle precipitate It was filtered

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a similar manner to Example 133, 4-tert-butoxycarbonylaminobicyclo[2.2.2]octane-1-carboxylic acid (150 mg) and 2-amino-5-chlorobenzotrifluoride (173 μL) were used to obtain 4-tert-butoxycarbonylamino-N-(4-chloro-2-trifluoromethylphenyl)bicyclo[2.2.2]octane-1-carboxamide (79.7 mg).

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-amino-5-chlorobenzotrifluoride (1.01 g, 5.16 mmol, Aldrich) in acetic anhydride (5 mL) was stirred at room temperature for 12 h to produce white needle precipitate. It was filtered to give 1.123 g (91.7%) of 2-acetamido-5-chlorobenzotrifluoride. 1H NMR (CDCl3): δ2.214 (s, 3H); 7.359 (br, 1H); 7.512 (d, 1H, J=9 Hz), 7.581 (s, 1H); 7.163 (d, 1H, J=8.4 Hz). to produce white needle precipitate It was filtered

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-amino-5-chlorobenzotrifluoride (1.01 g, 5.16 mmol, Aldrich) in acetic anhydride (5 mL) was stirred at room temperature for 12 h to produce white needle precipitate. It was filtered to give 1.123 g (91.7%) of 2-acetamido-5-chlorobenzotrifluoride. 1H NMR (CDCl3): δ 2.214 (S, 3H); 7.359 (br, 1H); 7.512 (d, 1H, J=9 Hz), 7.581 (s, 1H); 7.163 (d, 1H, J=8.4 Hz). to produce white needle precipitate It was filtered

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of sodium formate (38 parts) in water (100 parts) are added sodium hydroxide liquor (32%; 13.5 parts), benzyl triethylammonium chloride (1.0 parts), 3% palladium on charcoal (50% paste; 6.0 parts) and 5-chloro-2-aminobenzotrifluoride (19.6 parts). The mixture is stirred rapidly at the boil under reflux for 4 hours and then steam distilled. The distillate is extracted with chloroform (2 × 50 parts), the extract dried over magnesium sulphate and then the solvent removed to give 9.7 parts (60.3%) of 2-aminobenzotrifluoride. under reflux for 4 hours steam distilled The distillate is extracted with chloroform (2 × 50 parts) the extract dried over magnesium sulphate the solvent removed