반응 #670023

반응 방정식

2-fluoroaniline

hydrochloric acid

4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid

triethylamine

ethyl chloroformate

→

N-(2-fluorophenyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide

수율 64.9%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred for an additional 45 minutes
2. 2
   workup.STIRRINGto stir at ambient temperature for 14 hours
3. 3
   추출extracted 2× with ethyl acetate
4. 4
   세척The combined organic layers were washed with water
5. 5
   건조dried over magnesium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   workup.ADDITIONTo the residue was added aqueous 1N sodium hydroxide (10 mL) and ethyl alcohol (2 mL)
9. 9
   온도the mixture heated
10. 10
    온도at reflux for 4.5 hours
11. 11
    온도After cooling in an ice water bath
12. 12
    기타the precipitate collected
13. 13
    세척rinsed with water
14. 14
    기타dried
15. 15
    기타Recrystallization from ethyl alcohol

실험 절차

To a solution of 4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (538 mg, 3 mmol) and triethylamine (0.88 mL, 6.3 mmol) in N,N-dimethylformamide (15 mL) at 0° C. was added ethyl chloroformate (0.57 mL, 6 mmol). After stirring at 0° C. for 45 minutes, 2-fluoroaniline (0.58 mL, 6 mmol) wad added. The mixture was stirred for an additional 45 minutes, then allowed to stir at ambient temperature for 14 hours. The mixture was poured into aqueous 1.2N hydrochloric acid and extracted 2× with ethyl acetate. The combined organic layers were washed with water, dried over magnesium sulfate, filtered, and concentrated in vacuo. To the residue was added aqueous 1N sodium hydroxide (10 mL) and ethyl alcohol (2 mL) and the mixture heated at reflux for 4.5 hours. After cooling in an ice water bath, the mixture was acidified with aqueous hydrochloric acid, the precipitate collected, rinsed with water and dried. Recrystallization from ethyl alcohol afforded N-(2-fluorophenyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide (Compound 46) (530 mg). mp 238-240° C.

출처