Pyrrolidine → 4-Chloro-2-nitro-5-(1-pyrrolidinyl)aniline

Temperature

100 °C

Pyrrolidine (6 mL) was added to 4,5-dichloro-2-nitro-phenylamine (2.58 g, 12.5 mmol) in a sealed tube and the mixture heated to 100° C. for 6 h. The mixture was cooled to 23° C., poured into water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine (50 mL), dried, filtered, and concentrated under reduced pressure to afford the titled compound (3.00 g, 99%). MS (ESI/CI): mass calcd. for C10H12ClN3O2, 241.1; m/z found, 242.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.08 (s, 1H), 6.06 (s, 2H), 5.82 (s, 1H), 3.58 (ddd, J=6.6, 4.2, 2.7 Hz, 4H), 2.02-1.90 (m, 4H).

1. temperatureThe mixture was cooled to 23° C.
2. extractionextracted with EtOAc (3×100 mL)
3. washThe combined organic layers were washed with brine (50 mL)
4. customdried
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure

ORD record

ord-afcdbe30ac9c407fb26bf25772e8a2e0

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759345B2