methyl 2-amino-5-chloro-3-methoxybenzoate

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

Procedure: Methyl 2-amino-5-chloro-3-methoxybenzoate (770 mg, 3.57 mmol) was suspended in tetrahydrofuran (20 mL), 2M sodium hydroxide (5 mL) was added and the mixture was stirred at ambient temperature for 20 hours. The solution was concentrated in vacuo, then partitioned between ethyl acetate and 1M hydrochloric acid. The organic layer was washed with water, then brine, dried with sodium sulfate, decanted and concentrated in vacuo to yield 2-amino-5-chloro-3-methoxybenzoic acid. The solution was concentrated in vacuo partitioned between ethyl acetate and 1M hydrochloric acid The organic layer was washed with water brine, dried with sodium sulfate decanted concentrated in vacuo

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

Procedure: To methyl 2-amino-3-methoxybenzoate (750 mg, 4.1 mmol) in anhydrous N,N-dimethylformamide (15 mL) was added N-chlorosuccinimide (580 mg, 4.35 mmol) and this mixture was stirred at ambient temperature for 2 hours. The temperature was increased to 60° C. for 4 hours. The deep red solution was cooled, diluted with ethyl acetate, washed with saturated sodium bicarbonate, water, then brine, dried with sodium sulfate, decanted and concentrated to yield crude methyl 2-amino-5-chloro-3-methoxybenzoate (0.85 g, 95%). MS (m/z): 216.1 (M+H)+. The temperature was increased to 60° C. for 4 hours The deep red solution was cooled washed with saturated sodium bicarbonate, water brine, dried with sodium sulfate decanted concentrated