Synthesis
1. 2-Methoxy-4-nitrobenzonitrile (750 mg, 4.21 mmol) and palladium catalyst (50 mg, 0.47 mmol) were dissolved in methanol (15 mL) at room temperature. 2. The reaction system was subjected to a hydrogen atmosphere (1 atm) with continuous stirring for 48 h. 3. Upon completion of the reaction the palladium catalyst was removed by filtration. 4. The filtrate was concentrated under reduced pressure to give the brownish-red powdery product 4-amino-2-methoxybenzonitrile (679 mg, 4.58 mmol, quantitative yield). 5. The structure of the product was determined by 1H-anionic digestion. 6. The filtrate was concentrated under reduced pressure to give a brown-red powdery product, 4-amino-2-methoxybenzonitrile (679 mg, 4.58 mmol, quantitative yield). 5. The structure of the product was confirmed by 1H-NMR (300 MHz, DMSO-d6): δ 3.32 (3H, s), 6.05-6.29 (4H, m), 7.23 (1H, d, J = 8.3 Hz). ).
References
[1] Patent: EP2759533, 2014, A1. Location in patent: Paragraph 0484; 0485
[2] Synthesis, 2006, # 19, p. 3316 - 3340
[3] Chemistry - A European Journal, 2014, vol. 20, # 31, p. 9504 - 9509
[4] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 10, p. 979 - 988
[5] Patent: US2009/42967, 2009, A1. Location in patent: Page/Page column 22
