Hydrochloric Acid → Benzenamine, 4-methoxy-3-nitro-

Temperature

0 °C

To a 1M solution of 3-nitro-4-fluoroaniline (16.7 g, 107 mmol, from Aldrich Chemical Co., Milwaukee, Wis. USA) in anhydrous methanol at ambient temperature was added sodium methoxide (23.1 g, 428 mmol) and the resulting solution was refluxed with stirring for 21 hours. The reaction mixture was then cooled to 0° C. and a 12M solution of HCl (13.4 mL) was added dropwise followed by water (250 mL). The crude mixture was extracted three times with Et2O (200 mL). The organic layers were combined, washed with brine (300 mL), dried over Na2SO4, and concentrated under vacuum to yield 17.5 g (97%) of product as a dark brown solid, which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.09 (d, J=9 Hz, 1H), 7.01 (dd, J=2.8, 1.3 Hz, 1H), 6.85 (ddd, J=9, 2.8, 1.4 Hz, 1H), 5.2 (s, 2H), 3.75 (s, 3H).

1. temperaturethe resulting solution was refluxed
2. extractionThe crude mixture was extracted three times with Et2O (200 mL)
3. washwashed with brine (300 mL)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated under vacuum

ORD record

ord-4a81aeddec904fbfaabe0176e8d524fb

Source dataset

uspto-grants-2003_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06630513B1