methyl 2-(4-amino-2-chlorophenyl)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:; See reaction.notes.procedure_details.

Procedure: 2-(4 nitro-2-chlorophenyl )acetic acid methyl ester was reduced with tin chloride in methanol at reflux for 2 h. The solution was poured over ice and neutralized with saturated sodium bicarbonate. The mixture was extracted with methylene chloride, dried (MgSO4), and concentrated. The oil was purified by silica gel chromatography eluted with hexane/ethyl acetate(9:1 to 8:2) to yield the title compound (0.81 g). at reflux for 2 h The mixture was extracted with methylene chloride dried (MgSO4) concentrated The oil was purified by silica gel chromatography eluted with hexane/ethyl acetate(9:1 to 8:2)

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

Procedure: To a mixture of methyl 2-(4-amino-2-chlorophenyl)acetate (step 4, 2.6 g, 13.0 mmol) and 4,6-Dimethyl-3-nitro-2-pyridine (step 2 of Example 1, 2.4 g, 13.0 mmol) in DMSO was added diisopropylethylamine. The resulting mixture was stirred for 9 h at 50° C. To the mixture was poured into water and extracted with ethyl acetate (3×30 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated to give a brown oil. This was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1) to give 1.4 g (29%) of title compound as yellow solid. extracted with ethyl acetate (3×30 ml) The organic layer was washed with brine dried (MgSO4) concentrated to give a brown oil This was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1)

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

Procedure: To a mixture of methyl 2-(4-amino-2-chlorophenyl)acetate (step 4, 2.6 g, 13.0 mmol) and 4,6-Dimethyl-3-nitro-2-pyridine (step 2 of Example 1, 2.4 g, 13.0 mmol) in DMSO was added diisopropylethylamine. The resulting mixture was stirred for 9 h at 50° C. To the mixture was poured into water and extracted with ethyl acetate (3×30 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated to give a brown oil. This was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1) to give 1.4 g (29%) of title compound as yellow solid. extracted with ethyl acetate (3×30 ml) The organic layer was washed with brine dried (MgSO4) concentrated to give a brown oil This was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1)

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

Procedure: To a solution of methyl 2-(2-chloro-4-nitrophenyl)acetate (step 3, 3.6 g, 15.6 mmol) in ethanol/water (4/1) were added Fe (4.4 g, 78.0 mmol) and NH4Cl (409 mg, 7.8 mmol). The mixture was stirred for 1 h under reflux temperature. The solvent was removed and the residue was diluted with CH2Cl2. The mixture was washed with brine, dried (MgSO4) and concentrated to give 2.59 g (83%) of title compound as orange oil. under reflux temperature The solvent was removed the residue was diluted with CH2Cl2 The mixture was washed with brine dried (MgSO4) concentrated

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

Procedure: To a mixture of methyl 2-(4-amino-2-chlorophenyl)acetate (step 4, 2.6 g, 13.0 mmol) and 4,6-Dimethyl-3-nitro-2-pyridine (step 2 of Example 1, 2.4 g, 13.0 mmol) in DMSO was added diisopropylethylamine. The resulting mixture was stirred for 9 h at 50° C. To the mixture was poured into water and extracted with ethyl acetate (3×30 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated to give a brown oil. This was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1) to give 1.4 g (29%) of title compound as yellow solid. extracted with ethyl acetate (3×30 ml) The organic layer was washed with brine dried (MgSO4) concentrated to give a brown oil This was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1)

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

Procedure: To a solution of methyl 2-(2-chloro-4-nitrophenyl)acetate (step 3, 3.6 g, 15.6 mmol) in ethanol/water (4/1) were added Fe (4.4 g, 78.0 mmol) and NH4Cl (409 mg, 7.8 mmol). The mixture was stirred for 1 h under reflux temperature. The solvent was removed and the residue was diluted with CH2Cl2.The mixture was washed with brine, dried (MgSO4) and concentrated to give 2.59 g (83%) of title compound as orange oil. under reflux temperature The solvent was removed the residue was diluted with CH2Cl2 The mixture was washed with brine dried (MgSO4) concentrated

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

Procedure: To a solution of methyl 2-(2-chloro-4-nitrophenyl)acetate (step 3, 3.6 g, 15.6 mmol) in ethanol/water (4/1) were added Fe (4.4 g, 78.0 mmol) and NH4Cl (409 mg, 7.8 mmol). The mixture was stirred for 1 h under reflux temperature. The solvent was removed and the residue was diluted with CH2Cl2.The mixture was washed with brine, dried (MgSO4) and concentrated to give 2.59 g (83%) of title compound as orange oil. under reflux temperature The solvent was removed the residue was diluted with CH2Cl2 The mixture was washed with brine dried (MgSO4) concentrated

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

Procedure: To a mixture of methyl 2-(4-amino-2-chlorophenyl)acetate (step 4, 2.6 g, 13.0 mmol) and 4,6-Dimethyl-3-nitro-2-pyridine (step 2 of Example 1, 2.4 g, 13.0 mmol) in DMSO was added diisopropylethylamine. The resulting mixture was stirred for 9 h at 50° C. To the mixture was poured into water and extracted with ethyl acetate (3×30 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated to give a brown oil. This was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1) to give 1.4 g (29%) of title compound as yellow solid. extracted with ethyl acetate (3×30 ml) The organic layer was washed with brine dried (MgSO4) concentrated to give a brown oil This was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1)

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

Procedure: To a mixture of methyl 2-(4-amino-2-chlorophenyl)acetate (step 4, 2.6 g, 13.0 mmol) and 4,6-Dimethyl-3-nitro-2-pyridine (step 2 of Example 1, 2.4 g, 13.0 mmol) in DMSO was added diisopropylethylamine. The resulting mixture was stirred for 9 h at 50° C. To the mixture was poured into water and extracted with ethyl acetate (3×30 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated to give a brown oil. This was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1) to give 1.4 g (29%) of title compound as yellow solid. extracted with ethyl acetate (3×30 ml) The organic layer was washed with brine dried (MgSO4) concentrated to give a brown oil This was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1)

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

Procedure: To a mixture of methyl 2-(4-amino-2-chlorophenyl)acetate (step 4, 2.6 g, 13.0 mmol) and 4,6-Dimethyl-3-nitro-2-pyridine (step 2 of Example 1, 2.4 g, 13.0 mmol) in DMSO was added diisopropylethylamine. The resulting mixture was stirred for 9 h at 50° C. To the mixture was poured into water and extracted with ethyl acetate (3×30 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated to give a brown oil. This was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1) to give 1.4 g (29%) of title compound as yellow solid. extracted with ethyl acetate (3×30 ml) The organic layer was washed with brine dried (MgSO4) concentrated to give a brown oil This was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1)