Hydrochloric Acid → 2-Allyloxy-4-methoxyaniline

Temperature

80 °C

2.09 g of 2-allyloxy-4-methoxynitrobenzene was dissolved in 20 ml of ethanol, 5 ml of THF, and 4 ml of water. Thereafter, 4.27 g of ammonium chloride and 2.23 g of iron were added to the reaction solution, and the obtained mixture was stirred while heating at 80° C. for 4 hours. Thereafter, 2 g of ammonium chloride, 1 g of iron, and 0.25 ml of 5 N HCl were added to the reaction solution, and the obtained mixture was further stirred while heating for approximately 2 hours. The reaction solution was stood to cool and then filtered through celite. A saturated sodium bicarbonate aqueous solution and ethyl acetate were added thereto, so as to separate an organic layer. The obtained organic layer was washed with a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure, and the residue was then purified by NH silica gel column chromatography (hexane/ethyl acetate), so as to obtain 1.09 g of the subject compound.

1. stirringthe obtained mixture was further stirred
2. temperaturewhile heating for approximately 2 hours
3. temperatureto cool
4. filtrationfiltered through celite
5. additionA saturated sodium bicarbonate aqueous solution and ethyl acetate were added
6. customso as to separate an organic layer
7. washThe obtained organic layer was washed with a saturated sodium chloride solution
8. dry with materialdried over anhydrous magnesium sulfate
9. customAfter removing the drying agent
10. filtrationby filtration
11. concentrationthe organic layer was concentrated under a reduced pressure
12. customthe residue was then purified by NH silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-2e12f6eb102f4041bb915e4f8be842b7

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07538123B2