Réaction #78210

Équation de réaction

triethylamine

1-amino-4-bromonaphthalene

sodium hydroxide

methyl 4-amino-1-naphthalenecarboxylate

→

title compound

4-Amino-1-naphthalenecarboxylic acid

Solvants

dimethylformamide

methanol

ethanol

carbon monoxide

Conditions de réaction

Traitement

1. 1
   ConcentrationAfter the concentration under reduced pressure, water
2. 2
   workup.ADDITIONwas added to the reaction mixture
3. 3
   Extractionthe product was extracted with ethyl acetate
4. 4
   Concentrationconcentrated
5. 5
   Autrethus obtained
6. 6
   AutreEthanol was evaporated
7. 7
   Lavagethe residue was washed with ethyl acetate
8. 8
   ExtractionAfter the extraction with ethyl acetate
9. 9
   Lavagethe product was washed with water and saturated aqueous sodium chloride solution
10. 10
    Séchagedried over anhydrous sodium sulfate
11. 11
    Concentrationconcentrated under reduced pressure

Mode opératoire

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.

Source