2-NITRO-5-PYRROLIDIN-1-YL-PHENYLAMINE synthesis

Yield:289913-98-0 93%

Reaction Conditions:

for 6 h;Reflux;

Steps:

11

2-Nitro-5-(pyrrolidin-1-yl)benzenamine: A mixture of 5-chloro-2-nitroaniline (1.73 g, 10 mmol) and pyrrolidine (1.42 g, 20 mmole) was refluxed in a pressure vessel for 6 h. Solvent was evaporated and the residue was diluted with ethyl acetate. The resulting mixture was washed with aqueous NaHCO₃ (5%) and distilled water, dried over MgSO₄, and concentrated to afford 2-nitro-5-(pyrrolidin-1-yl)benzenamine as a solid (93% yield). ¹H NMR (400 MHz, CDCl₃) δ (ppm): 7.80 (d, J=8 Hz, 1H, 3-H), 7.22 (s, 2H, NH₂), 6.05 (dd, J=8, 2 Hz, 1H, 4-H), 5.81 (d, J=2 Hz, 1H, 6-H), 3.30-3.27 (m, 4H, 2',5'-H), 1.97-1.91 (m, 4H, 3',4'-H). ¹³C NMR (100 MHz, CDCl₃-d₁) δ (ppm): 151.9, 148.3, 127.4, 122.1, 104.7, 94.5, 47.3, 47.3, 24.8, 24.8; EIMS: m/z 207 (M⁺).

References:

US2010/179147,2010,A1 Location in patent:Page/Page column 10