39061-72-8

1. In a reaction flask, 1-(4-chloro-2-nitrophenyl)ethanone (5.0 g, 25 mmol) and iron powder (5.6 g, 100 mmol) were suspended in a solvent mixture of acetic acid (50 mL) and water (50 mL). 2. The reaction mixture was heated to reflux with continuous stirring for 16 h. 3. Upon completion of the reaction, the mixture was cooled to room temperature. 4. The reaction mixture was neutralized with a saturated aqueous sodium bicarbonate solution. 5. The mixture was extracted three times with ethyl acetate. 6. The organic layers were combined and washed sequentially with saturated aqueous sodium bicarbonate and brine. 7. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate. 5. The mixture was extracted with ethyl acetate three times. 6. The organic layers were combined and washed with saturated aqueous sodium bicarbonate and brine in that order. 7. The organic layers were dried with anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. 8. The residue was purified by silica gel fast column chromatography (eluent: ethyl acetate/petroleum ether=1:4) to give the target product 1-(2-amino-4-chlorophenyl)ethanone, and the target product 1-(2-amino-4- chlorophenyl)ethanone was obtained by fast column chromatography on silica gel. chlorophenyl)ethanone (3.8 g, 89% yield) as a yellow solid.

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7381 - 7387
[2] Patent: WO2015/54572, 2015, A1. Location in patent: Page/Page column 274
[3] Journal of the Chemical Society [Section] C: Organic, 1968, p. 2747 - 2751
[4] Patent: US4379929, 1983, A
[5] Patent: US2008/287458, 2008, A1. Location in patent: Page/Page column 39