1-N,1-N-diethyl-2-fluorobenzene-1,4-diamine

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

Procedure: To a solution of N1,N1-diethyl-2-fluorobenzene-1,4-diamine (1.50 g, 8.23 mmol) in anhydrous CH2Cl2 (60 mL) was added trimethylaluminium (33 mL, 33 mmol, 1 M in heptane) dropwise slowly under N2. Upon the end of addition the mixture was stirred at rt for 40 min. To this mixture was added a solution of methyl 3-acetaminocrotonate (2.58 g, 16.40 mmol) in anhydrous CH2Cl2 (20 mL). The resulting reaction mixture was stirred at rt for another 6 h, then quenched with water. The organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was recrystallized from EtOAc to give the title compound as a pale yellow solid (1.60 g, 67%). The compound was characterized by the following spectroscopic data: Upon the end of addition the mixture The resulting reaction mixture was stirred at rt for another 6 h quenched with water The organic phase was washed with brine dried over anhydrous Na2SO4 concentrated in vacuo The crude product was recrystallized from EtOAc

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

Procedure: To a solution of N,N-diethyl-2-fluoro-4-nitroaniline (4.00 g, 18.84 mmol) in THF (50 mL) was added Pd/C (1.50 g). The reaction mixture was stirred at rt under H2 for 12 h. The mixture was filtered, and the filtrate was concentrated in vacuo to give the title compound as an offwhite solid (3.20 g, 93%). The mixture was filtered the filtrate was concentrated in vacuo

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

Procedure: To a solution of N1,N1-diethyl-2-fluorobenzene-1,4-diamine (1.50 g, 8.23 mmol) in anhydrous CH2Cl2 (60 mL) was added trimethylaluminium (33 mL, 33 mmol, 1 M in heptane) dropwise slowly under N2. Upon the end of addition the mixture was stirred at rt for 40 min. To this mixture was added a solution of methyl 3-acetaminocrotonate (2.58 g, 16.40 mmol) in anhydrous CH2Cl2 (20 mL). The resulting reaction mixture was stirred at rt for another 6 h, then quenched with water. The organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was recrystallized from EtOAc to give the title compound as a pale yellow solid (1.60 g, 67%). The compound was characterized by the following spectroscopic data: Upon the end of addition the mixture The resulting reaction mixture was stirred at rt for another 6 h quenched with water The organic phase was washed with brine dried over anhydrous Na2SO4 concentrated in vacuo The crude product was recrystallized from EtOAc

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

Procedure: To a solution of N,N-diethyl-2-fluoro-4-nitroaniline (4.00 g, 18.84 mmol) in THF (50 mL) was added Pd/C (1.50 g). The reaction mixture was stirred at rt under H2 for 12 h. The mixture was filtered, and the filtrate was concentrated in vacuo to give the title compound as an offwhite solid (3.20 g, 93%). The mixture was filtered the filtrate was concentrated in vacuo

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

Procedure: To a solution of N1,N1-diethyl-2-fluorobenzene-1,4-diamine (1.50 g, 8.23 mmol) in anhydrous CH2Cl2 (60 mL) was added trimethylaluminium (33 mL, 33 mmol, 1 M in heptane) dropwise slowly under N2. Upon the end of addition the mixture was stirred at rt for 40 min. To this mixture was added a solution of methyl 3-acetaminocrotonate (2.58 g, 16.40 mmol) in anhydrous CH2Cl2 (20 mL). The resulting reaction mixture was stirred at rt for another 6 h, then quenched with water. The organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was recrystallized from EtOAc to give the title compound as a pale yellow solid (1.60 g, 67%). The compound was characterized by the following spectroscopic data: Upon the end of addition the mixture The resulting reaction mixture was stirred at rt for another 6 h quenched with water The organic phase was washed with brine dried over anhydrous Na2SO4 concentrated in vacuo The crude product was recrystallized from EtOAc

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

Procedure: To a solution of N,N-diethyl-2-fluoro-4-nitroaniline (4.00 g, 18.84 mmol) in THF (50 mL) was added Pd/C (1.50 g). The reaction mixture was stirred at rt under H2 for 12 h. The mixture was filtered, and the filtrate was concentrated in vacuo to give the title compound as an offwhite solid (3.20 g, 93%). The mixture was filtered the filtrate was concentrated in vacuo