Methyl iodide → 2-chloro-N-methyl-5-nitroaniline

To a suspension of sodium hydride (60% in oil, 1.2 g, 30 mmol) in tetrahydrofuran (100 ml), cooled in an ice bath, was added slowly a solution of 2-chloro-5-nitroaniline (5 g, 29 mmol) in tetrahydrofuran (10 ml) followed by a solution of iodomethane (1.8 ml, 29 mmol) in tetrahydrofuran (10 ml). After stirring at room temperature for 20 hours, the mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (100 ml) and water (100 ml). The organic layer was washed with saturated aqueous sodium chloride solution (50 ml), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane-hexane (1:3) and recrystallized (ethyl ether) to provide (2-chloro-5-nitro-phenyl)-methyl-amine (1.8 g, 33% yield) as orange crystals.

1. temperaturecooled in an ice bath
2. concentrationthe mixture was concentrated under reduced pressure
3. customthe residue was partitioned between dichloromethane (100 ml) and water (100 ml)
4. washThe organic layer was washed with saturated aqueous sodium chloride solution (50 ml)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane-hexane (1:3)
8. customrecrystallized (ethyl ether)

ORD record

ord-dff35f989b9345fb86ab6ec382ca30c9

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07618968B2