Benzyl-(2-chloro-3-nitro-6-trifluoromethyl-pyridin-4-yl)-amine → N4-Benzyl-2-chloro-6-trifluoromethyl-pyridine-3,4-diamine

Benzyl-(2-chloro-3-nitro-6-trifluoromethyl-pyridine-4-yl)-amine (345 mg, 1.0 mmol) was dissolved in a mixture of AcOH (18 ml) and water (2 ml). Fe powder (349 mg, 6.2 mmol) was added and the mixture was vigorously stirred at room temperature for 24 h. The reaction mixture was concentrated in vacuo and the residue was diluted with EtOAc (10 ml) and water (10 ml). The mixture was filtered through celite, washing through with EtOAc (20 ml). The layers were separated and the organic layer was washed with sat. NaHCO3 (aq) (2×10 ml) and brine (10 ml), dried over MgSO4 and concentrated in vacuo to give the title compound (304 g) as a pale yellow solid.

1. concentrationThe reaction mixture was concentrated in vacuo
2. additionthe residue was diluted with EtOAc (10 ml) and water (10 ml)
3. filtrationThe mixture was filtered through celite
4. washwashing through with EtOAc (20 ml)
5. customThe layers were separated
6. washthe organic layer was washed with sat. NaHCO3 (aq) (2×10 ml) and brine (10 ml)
7. dry with materialdried over MgSO4
8. concentrationconcentrated in vacuo

ORD record

ord-a7fde78db8554c5db0557ec9b6f396e9

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691877B2