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The general procedure for the synthesis of 2-chloro-4-methoxyaniline from 2-chloro-4-methoxynitrobenzene was as follows: iron powder (5.10 g, 91.69 mmol) was added to a water (22 mL) and methanol (70 mL) containing 2-chloro-4-methoxy-1-nitrobenzene (1.72 g, 9.17 mmol) and ammonium chloride (1.96 g, 36.68 mmol) in a ) in a mixed suspension. The reaction mixture was heated to 50 °C and stirred at this temperature for 1 hour. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the solid was washed with distilled water (2 x 15 mL). The filtrate was extracted with ethyl acetate (2 x 50 mL) and the combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography (eluent: 10-22% ethyl acetate/hexane) to afford 2-chloro-4-methoxyaniline (orange oil, 1.24 g, 86% yield).HPLC-MS (Method A): retention time 7.37 min; ESI-MS m/z: 158 ([M+H]+).

[1] Patent: WO2018/13774, 2018, A1. Location in patent: Page/Page column 455
[2] Patent: WO2018/1973, 2018, A1. Location in patent: Page/Page column 196
[3] Journal of the Chemical Society, 1927, p. 2218
[4] Journal of the Chemical Society, 1928, p. 331
[5] Journal of the Chemical Society, 1927, p. 2218