反应详情

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (22.2 g, 115 mmol) was added to a solution of 2,6-naphthalenedicarboxylic acid (25 g, 115 mmol) and hydroxybenzotriazole (15.6 g, 115 mmol) in dimethylformamide (1800 ml) and the mixture was stirred at room temperature for 2 hours. Diethyl amine (34.3 ml, 345 mmol) was added and the solution was stirred overnight at room temperature. The solvent was then evaporated under reduced pressure and the crude was treated with 1N HCl (500 ml) and ethyl acetate (500 ml), insoluble compounds were filtered off and the phases were separated. The organic phase was extracted with 5% sodium carbonate (3×200 ml) and the combined aqueous solutions were acidified with concentrated HCl and extracted with ethyl acetate (3×200 ml). The organic solution was then washed with 1N HCl (6×100 ml), dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure yielding 18.5 g (Yield 60%) of pure 6-(diethylaminocarbonyl)-2-naphthalenecarboxylic acid; m.p.=122-124° C.

1. stirringthe solution was stirred overnight at room temperature
2. customThe solvent was then evaporated under reduced pressure
3. additionthe crude was treated with 1N HCl (500 ml) and ethyl acetate (500 ml), insoluble compounds
4. filtrationwere filtered off
5. customthe phases were separated
6. extractionThe organic phase was extracted with 5% sodium carbonate (3×200 ml)
7. extractionextracted with ethyl acetate (3×200 ml)
8. washThe organic solution was then washed with 1N HCl (6×100 ml)
9. dry with materialdried over anhydrous sodium sulphate
10. customthe solvent was removed under reduced pressure