Reaktion #78210

Reaktionsgleichung

triethylamine

1-amino-4-bromonaphthalene

sodium hydroxide

methyl 4-amino-1-naphthalenecarboxylate

→

title compound

4-Amino-1-naphthalenecarboxylic acid

Lösungsmittel

dimethylformamide

methanol

ethanol

carbon monoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter the concentration under reduced pressure, water
2. 2
   workup.ADDITIONwas added to the reaction mixture
3. 3
   Extraktionthe product was extracted with ethyl acetate
4. 4
   Einengenconcentrated
5. 5
   Sonstigethus obtained
6. 6
   SonstigeEthanol was evaporated
7. 7
   Waschenthe residue was washed with ethyl acetate
8. 8
   ExtraktionAfter the extraction with ethyl acetate
9. 9
   Waschenthe product was washed with water and saturated aqueous sodium chloride solution
10. 10
    Trocknendried over anhydrous sodium sulfate
11. 11
    Einengenconcentrated under reduced pressure

Vorschrift

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.

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