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5-AMino-2,4-dichloro-benzoic acid Methyl ester synthesis

3synthesis methods
101495-62-9 Synthesis
2,4-Dichloro-5-nitro-benzoic acid Methyl ester

101495-62-9
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Yield:84228-48-8 66%

Reaction Conditions:

with hydroxylamine hydrochloride;iron in methanol;water at 90; for 18 h;Inert atmosphere;

Steps:

Intermediate R: Methyl 5-amino-2,4-dichlorobenzoate

A mixture of Intermediate Q (580.0 mg, 2.32 mmol), iron powder (259.0 mg, 4.64 mmol), ammonium chloride (869.0 mg, 16.24 mmol), methanol (1.55 mL) and water (3.09 mL) was purged with nitrogen and heated to 90 00 for 18 h. The crude solution was filtered through a pad of Celite , eluting with 50% EtOAc in petroleum ether to afford a filtrate which was then dried with Na2SO4, filtered and concentrated under reduced pressure to afford the title compound as an orange solid (339.0 mg, 66%). 1H NMR OH (ODd3, 500 MHz) 7.35 (s, 1H), 7.26 (s, 1H), 3.90 (s, 3H). LCMS (Method C): 2.70 mm (220.0, [M+H]).

References:

WO2018/122559,2018,A1 Location in patent:Page/Page column 37; 38