ethyl 2-(4-chloroanilino)acetate

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

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

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: 4-Chloroaniline (2.0 g) was dissolved in acetonitrile (20 ml), and ethyl bromoacetate (2.1 g) and potassium carbonate (2.2 g) were added to stir the mixture at 60° C. for 2 days. The reaction mixture was filtered through Celite pad, and the filtrate was concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel (hexane:chloroform=2:1) to obtain the title compound (2.3 g). The reaction mixture was filtered through Celite pad the filtrate was concentrated under reduced pressure The resultant residue was purified by column chromatography on silica gel (hexane:chloroform=2:1)

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

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of ethyl 2-((4-chlorophenyl)amino)acetate (10.0 g, 46.8 mmol) and (E)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (11.0 g, 65.5 mmol) in DCM (150 mL) was heated overnight at 50° C. The resulting mixture was concentrated and then triturated with 20% EtOAc/heptane and the resulting solid filtered and washed with heptane to yield (E)-ethyl 2-((4-chlorophenyl)(4,4,4-trifluoro-3-oxobut-1-en-1-yl)amino)acetate. The resulting mixture was concentrated triturated with 20% EtOAc/heptane the resulting solid filtered washed with heptane

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

Procedure: A mixture of 4-chloroaniline (12.8 g, 100.3 mmol), ethyl bromoacetate (12.2 mL, 110.4 mmol). and potassium carbonate (13.9 g, 100.3 mmol) in acetonitrile (330 mL) was heated overnight at 80° C. The resulting mixture was cooled to room temperature and filtered. The filtrate was concentrated and triturated DCM and the resulting solid was filtered to yield ethyl 2-((4-chlorophenyl)amino)acetate. filtered The filtrate was concentrated triturated DCM the resulting solid was filtered

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

Procedure: 4-Chloroaniline (2.0 g) was dissolved in acetonitrile (20 mL), and bromoethyl acetate (2.1 g) and potassium carbonate (2.2 g) were added thereto, followed by stirring at 60° C. for 2 days. The reaction mixture was filtered through a Celite pad, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:chloroform=2:1), to thereby give the title compound (2.3 g). The reaction mixture was filtered through a Celite pad the filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane:chloroform=2:1)

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

Procedure: Ethyl 2-(4-chlorophenylamino)acetate (A) (25.6 g, 120 mmol) and hydrazine monohydrate (7.0 mL, 144 mmol) were heated to reflux in ethanol (120 mL) for 22 hours. After concentration in vacuo, the solid obtained was recrystallised from ethanol to yield the title compound (14.0 g, 59%) as a pale brown powder. 1H NMR (400 MHz, CDCl3) δ 3.85 (2H, d), 4.18 (2H, br), 6.53 (2H, d), 7.16 (2H, d), 7.60 (1H, br). After concentration in vacuo the solid obtained was recrystallised from ethanol

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

Procedure: 4-Chloroaniline (15.5 g, 122 mmol), ethyl iodoacetate (14.4 mL, 122 mmol) and sodium acetate (20.0 g, 244 mmol) were stirred in water (24 mL) at 90° C. for 3 hours. After cooling to room temperature the precipitate was collected by filtration, washing with water (40 mL), to yield the title compound (25.6 g, 98%) as brown prisms. 1H NMR (400 MHz, CDCl3) δ 1.29 (3H, t), 3.86 (2H, s), 4.22 (2H, q), 6.53 (2H, d), 7.14 (2H, d). was collected by filtration washing with water (40 mL)

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of ethyl 2-((4-chlorophenyl)amino)acetate (10.0 g, 46.8 mmol) and (E)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (11.0 g, 65.5 mmol) in DCM (150 mL) was heated overnight at 50° C. The resulting mixture was concentrated and then triturated with 20% EtOAc/heptane and the resulting solid filtered and washed with heptane to yield (E)-ethyl 2-((4-chlorophenyl)(4,4,4-trifluoro-3-oxobut-1-en-1-yl)amino)acetate. The resulting mixture was concentrated triturated with 20% EtOAc/heptane the resulting solid filtered washed with heptane