Methyl 2-(2-methyl-5-nitrophenyl)acetate → Methyl 2-(5-amino-2-methylphenyl)acetate

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2-(2-Methyl-5-nitrophenyl)acetic acid methyl ester 14 (32 g, 153 mmol) was dissolved in ethanol (750 mL). To this solution was added 10% palladium on carbon (3.2 g). After the mixture was degassed, a balloon filled with hydrogen was fitted. The reaction was stirred at rt for 16 h. After removing the catalyst by filtering through a celite plug and removing the solvent in vacuo, the crude product was purified using flash chromatography (ethyl acetate:petroleum ether=5:1). The product 7 was isolated as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 6.9 (d, J=7.8 Hz), 6.59 (m, 1H), 6.56 (m, 1H), 3.69 (s, 3H).

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