Iodine → N-Methyl-2-(2-nitrophenyl)ethan-1-amine

Temperature

0 °C

At 0° C., a solution of N-methyl-2-(2-nitrophenyl)acetamide (7.00 g, 36.05 mmol) in tetrahydrofuran (410 ml) was added dropwise to a suspension of sodium borohydride (1.63 g, 43.25 mmol) in tetrahydrofuran (110 ml). A solution of iodine (4.57 g, 18.02 mmol) in tetrahydrofuran (150 ml) was added dropwise. The reaction mixture was warmed to reflux for 16 h. It was cooled to 0° C. Methanol (310 ml) was added dropwise. The solvent was removed in vacuo. The residue was dissolved in 20% aqueous sodium hydoxide solution (300 ml) and tert-butyl methyl ether (200 ml). The phases were separated. The aqueous phase was extracted with tert-butyl methyl ether (2×100 ml). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (160 g), using dichloromethane/methanol/25% aqueous ammonia (100:10:1) as eluent, to give 1.28 g of N-methyl-N-(2-(2-nitrophenyl)ethyl)amine.

1. temperatureThe reaction mixture was warmed
2. temperatureto reflux for 16 h
3. customThe solvent was removed in vacuo
4. dissolutionThe residue was dissolved in 20% aqueous sodium hydoxide solution (300 ml)
5. customThe phases were separated
6. extractionThe aqueous phase was extracted with tert-butyl methyl ether (2×100 ml)
7. dry with materialThe combined organic layers were dried over magnesium sulfate
8. customThe solvent was removed in vacuo
9. customThe crude product was purified by flash chromatography on silica (160 g)

ORD record

ord-120f3c106bd94f1b860054ef0572536c

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06127354