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N-(3-Chloro-2-nitrophenyl)glycine (12). 3-Chloro-2-nitroaniline (5.12 g, 29.7 mmol) was heated with bromoacetic acid (4.25 g, 29.7 mmol) at 125 ¡ãC for 1 h with air passing over the mixture to remove the HBr. Methanol was then added
and the mixture heated until all the solid dissolved. Dilute NH4OH was added in portions to maintain the pH > 8 while the mixture was concentrated by heating. The cooled mixture was filtered and then washed with dilute NH4OH, and the
filtrate was washed with ether (50 mL). The aqueous layer was then concentrated to a small volume and acidified while hot to pH 3 with concentrated HCl. After cooling, the product was collected, washed with ice-water, and dried to give 12 as
a yellow-brown solid: mp 195-197 ¡ãC (dec). Additional product was obtained by extracting the filtrate with AcOEt (2 *25 mL) and washing the extracts with saturated NaCl (25 mL). After the extract was dried (MgSO4), it was concentrated togive a yellow solid (total 0.42 g, 6% total yield)¡£
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