Acetone → (2-Amino-3-chlorophenyl)amine

Temperature

23 °C

To a solution of 3-chloro-2-nitro-phenylamine (1.73 g, 10.0 mmol), NH4Cl (2.68 g, 50.0 mmol), acetone (40 mL) and water (10 mL), was added zinc powder portion-wise (three equal portions over 5 minutes) (3.26 g, 50.0 mmol) at 0° C. The mixture was stirred for 2 h then warmed to 23° C. The mixture was filtered through Celite® and the solvents were concentrated under reduced pressure. The mixture was re-dissolved in EtOAc/DCM and filtered a second time through Celite® and the solvents were evaporated. The crude mixture was diluted with EtOAc (100 mL), washed with brine (40 mL), dried, filtered, and concentrated under reduced pressure. The residue was purified (FCC) (10-50% EtOAc/hexanes) to yield the titled compound (1.00 g, 70%). MS (ESI/CI): mass calcd. for C6H7ClN2, 142.0; m/z found, 143.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 6.86-6.78 (m, 1H), 6.65-6.58 (m, 2H), 3.74 (br s, 2H), 3.46 (br s, 2H).

1. filtrationThe mixture was filtered through Celite®
2. concentrationthe solvents were concentrated under reduced pressure
3. dissolutionThe mixture was re-dissolved in EtOAc/DCM
4. filtrationfiltered a second time through Celite®
5. customthe solvents were evaporated
6. additionThe crude mixture was diluted with EtOAc (100 mL)
7. washwashed with brine (40 mL)
8. customdried
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified (FCC) (10-50% EtOAc/hexanes)

ORD record

ord-f927db23646e4b929cbfa79272daf6b8

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759345B2