Iodoethane → 3-Methoxynaphthalen-2-amine

3-Amino-2-naphthol (7.96 g, 50.0 mmol) was dissolved in N-methylpyrrolidone (190 ml), and the mixture was stirred under ice-cooling. Then, 60% sodium hydride (2.08 g, 52 mmol) was added, and the mixture was stirred at the same temperature for 40 min. Then, ethyl iodide (3.3 ml, 53 mmol) was added, and the mixture was stirred at the same temperature for 2 hr. To the reaction mixture was added diluted aqueous sodium hydroxide solution, and the mixture was extracted with an ethyl acetate-hexane=1:1 mixed solvent. The organic layer was washed with diluted aqueous sodium hydroxide solution, water and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane), and the obtained solid was washed with hexane and dried under reduced pressure to give the title compound (4.53 g, yield 52%) as a colorless solid.

1. temperaturecooling
2. stirringthe mixture was stirred at the same temperature for 40 min
3. stirringthe mixture was stirred at the same temperature for 2 hr
4. extractionthe mixture was extracted with an ethyl acetate-hexane=1:1 mixed solvent
5. washThe organic layer was washed with diluted aqueous sodium hydroxide solution, water and saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationThe insoluble material was filtered off
8. concentrationthe solution was concentrated under reduced pressure
9. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)
10. washthe obtained solid was washed with hexane
11. customdried under reduced pressure

ORD record

ord-5c590797463b489881f00ba923278708

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513235B2