반응 #78210

반응 방정식

triethylamine

1-amino-4-bromonaphthalene

sodium hydroxide

methyl 4-amino-1-naphthalenecarboxylate

→

title compound

4-Amino-1-naphthalenecarboxylic acid

용매

dimethylformamide

methanol

ethanol

carbon monoxide

반응 조건

후처리

1. 1
   농축After the concentration under reduced pressure, water
2. 2
   workup.ADDITIONwas added to the reaction mixture
3. 3
   추출the product was extracted with ethyl acetate
4. 4
   농축concentrated
5. 5
   기타thus obtained
6. 6
   기타Ethanol was evaporated
7. 7
   세척the residue was washed with ethyl acetate
8. 8
   추출After the extraction with ethyl acetate
9. 9
   세척the product was washed with water and saturated aqueous sodium chloride solution
10. 10
    건조dried over anhydrous sodium sulfate
11. 11
    농축concentrated under reduced pressure

실험 절차

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.

출처