Triethylamine → 4-Amino-1-naphthoic acid

Temperatur

80 °C

1.60 g (2.3 mmol) of bis(triphenylphosphine)dichloropalladium, 7.0 ml (50.6 mmol) of triethylamine and 60 ml of methanol were successively added to a mixture of 5.00 g (22.5 mmol) of 1-amino-4-bromonaphthalene and 60 ml of dimethylformamide, and they were stirred in carbon monoxide atmosphere at 80° C. for 2 days. After the concentration under reduced pressure, water was added to the reaction mixture and the product was extracted with ethyl acetate and concentrated. 20 ml of ethanol and 10 ml (40.0 mmol) of 4 N aqueous sodium hydroxide solution were added to crude methyl 4-amino-1-naphthalenecarboxylate thus obtained. They were stirred at 80° C. overnight. Ethanol was evaporated, and the residue was washed with ethyl acetate. The aqueous layer was neutralized with hydrochloric acid. After the extraction with ethyl acetate, the product was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound.

1. concentrationAfter the concentration under reduced pressure, water
2. additionwas added to the reaction mixture
3. extractionthe product was extracted with ethyl acetate
4. concentrationconcentrated
5. customthus obtained
6. customEthanol was evaporated
7. washthe residue was washed with ethyl acetate
8. extractionAfter the extraction with ethyl acetate
9. washthe product was washed with water and saturated aqueous sodium chloride solution
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-5698eedece90432c9b83a625bb4512b2

Quelldatensatz

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06710056B2