2,4,5-trifluoro-3-methoxyaniline

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

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50 ml of water and 200 ml of concentrated sulfuric acid were added to 84.4 g (0.42 mole) of 2-amino-4-methoxy-3,5,6-trifluorobenzonitrile (XX) [prepared as described in Step (E2) above]. The mixture was then stirred at 100° C. for 1 hour, after which 150 ml of water were added thereto, and the mixture was stirred at 110°-120° C. for a further 2 hours. The reaction mixture was then allowed to stand to cool to room temperature, after which it was poured into ice-water and neutralized with potassium carbonate. The crystalline substance which precipitated was extracted with ethyl acetate; the extract was washed with water and dried over anhydrous sodium sulfate; and the solvent was removed by evaporation under reduced pressure to afford 57.6 g of 3-methoxy-2,4,5-trifluoroaniline (XXIII) as colorless needles melting at 45°-47° C. the mixture was stirred at 110°-120° C. for a further 2 hours to cool to room temperature The crystalline substance which precipitated was extracted with ethyl acetate the extract was washed with water dried over anhydrous sodium sulfate and the solvent was removed by evaporation under reduced pressure

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

Procedure: 1.1 g (0.02 mole) of hydrazine hydrate was added to a suspension of 2.15 g (0.007 mole) of N-(3-methoxy-2,4,5-trifluorophenyl)phthalimide (XXXVI) [prepared as described in Step (F3) above] in 30 ml of ethanol, and the mixture was heated under reflux with stirring for 2 hours. The reaction mixture was cooled to room temperature and then filtered. The filtrate was concentrated by evaporation under reduced pressure, and the residue was dissolved in toluene. The resulting solution was washed with water and dried, and the solvent was then removed by evaporation under reduced pressure to afford 1.06 g of 3-methoxy-2,4,5-trifluoroaniline (XXIII) as pale brown needles. the mixture was heated under reflux filtered The filtrate was concentrated by evaporation under reduced pressure the residue was dissolved in toluene The resulting solution was washed with water dried the solvent was then removed by evaporation under reduced pressure

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50 ml of water and 200 ml of concentrated sulfuric acid were added to 84.4 g (0.42 mole) of 2-amino-4-methoxy-3,5,6-trifluorobenzonitrile (XX) [prepared as described in Step (E2) above]. The mixture was then stirred at 100° C. for 1 hour, after which 150 ml of water were added thereto, and the mixture was stirred at 110°-120° C. for a further 2 hours. The reaction mixture was then allowed to stand to cool to room temperature, after which it was poured into ice-water and neutralized with potassium carbonate. The crystalline substance which precipitated was extracted with ethyl acetate; the extract was washed with water and dried over anhydrous sodium sulfate; and the solvent was removed by evaporation under reduced pressure to afford 57.6 g of 3-methoxy-2,4,5-trifluoroaniline (XXIII) as colorless needles melting at 45°-47° C. the mixture was stirred at 110°-120° C. for a further 2 hours to cool to room temperature The crystalline substance which precipitated was extracted with ethyl acetate the extract was washed with water dried over anhydrous sodium sulfate and the solvent was removed by evaporation under reduced pressure

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

Procedure: 1.1 g (0.02 mole) of hydrazine hydrate was added to a suspension of 2.15 g (0.007 mole) of N-(3-methoxy-2,4,5-trifluorophenyl)phthalimide (XXXVI) [prepared as described in Step (F3) above] in 30 ml of ethanol, and the mixture was heated under reflux with stirring for 2 hours. The reaction mixture was cooled to room temperature and then filtered. The filtrate was concentrated by evaporation under reduced pressure, and the residue was dissolved in toluene. The resulting solution was washed with water and dried, and the solvent was then removed by evaporation under reduced pressure to afford 1.06 g of 3-methoxy-2,4,5-trifluoroaniline (XXIII) as pale brown needles. the mixture was heated under reflux filtered The filtrate was concentrated by evaporation under reduced pressure the residue was dissolved in toluene The resulting solution was washed with water dried the solvent was then removed by evaporation under reduced pressure

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

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50 ml of water and 200 ml of concentrated sulfuric acid were added to 84.4 g (0.42 mole) of 2-amino-4-methoxy-3,5,6-trifluorobenzonitrile (XX) [prepared as described in Step (E2) above]. The mixture was then stirred at 100° C. for 1 hour, after which 150 ml of water were added thereto, and the mixture was stirred at 110°-120° C. for a further 2 hours. The reaction mixture was then allowed to stand to cool to room temperature, after which it was poured into ice-water and neutralized with potassium carbonate. The crystalline substance which precipitated was extracted with ethyl acetate; the extract was washed with water and dried over anhydrous sodium sulfate; and the solvent was removed by evaporation under reduced pressure to afford 57.6 g of 3-methoxy-2,4,5-trifluoroaniline (XXIII) as colorless needles melting at 45°-47° C. the mixture was stirred at 110°-120° C. for a further 2 hours to cool to room temperature The crystalline substance which precipitated was extracted with ethyl acetate the extract was washed with water dried over anhydrous sodium sulfate and the solvent was removed by evaporation under reduced pressure

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

Procedure: 1.1 g (0.02 mole) of hydrazine hydrate was added to a suspension of 2.15 g (0.007 mole) of N-(3-methoxy-2,4,5-trifluorophenyl)phthalimide (XXXVI) [prepared as described in Step (F3) above] in 30 ml of ethanol, and the mixture was heated under reflux with stirring for 2 hours. The reaction mixture was cooled to room temperature and then filtered. The filtrate was concentrated by evaporation under reduced pressure, and the residue was dissolved in toluene. The resulting solution was washed with water and dried, and the solvent was then removed by evaporation under reduced pressure to afford 1.06 g of 3-methoxy-2,4,5-trifluoroaniline (XXIII) as pale brown needles. the mixture was heated under reflux filtered The filtrate was concentrated by evaporation under reduced pressure the residue was dissolved in toluene The resulting solution was washed with water dried the solvent was then removed by evaporation under reduced pressure

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