Hydrochloric Acid → HCID 10263984, 화합물

HRID 1741665노트

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HRID 1741665 반응식
[C:1]([C:4](C(O)=O)([CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)[CH2:5][C:6]([OH:8])=[O:7])([OH:3])=[O:2].Cl.S([O-])([O-])(=O)=O.[Na+].[Na+]>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[C:1]([CH:4]([CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)[CH2:5][C:6]([OH:8])=[O:7])([OH:3])=[O:2]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 24436Sodium SulfateHCID 104243533,3-Dicarboxy-4-(indol-3-yl)butanoic acid

생성물 1

HCID 10263984HCID 10263984, 화합물

시약·촉매·용매 2

HCID 23978Copper촉매HCID 7047Quinoline용매

반응 조건

온도
145 °C

실험 절차

3,3-Dicarboxy-4-(indol-3-yl)butanoic acid (10.0 g) was dissolved in freshly distilled quinoline (50 ml) under dry nitrogen and copper powder (1.0 g, 40-80 mesh) was added. The reaction mixture was treated with ultrasound for 0.5 hours and heated to 125° C. for 0.75 hours and 145° C. for 1 hour. The reaction was cooled and poured onto ice, acidified with 5N hydrochloric acid and saturated with sodium sulphate. The mixture was extracted with ethyl acetate (4×100 ml). The combined organic extract was extracted with 5% sodium bicarbonate solution and the combined aqueous extract was poured onto ice, acidified with 5N hydrochloric acid, saturated with sodium sulphate and extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and evaporated. The resulting oil was taken up into 1,2 dichloroethane and heated and scratched to induce crystallisation. Filtration gave the title compound as white crystals, mp 144°-145° C.; found: C, 62.93; H, 5.48; N 5.62; C13H13NO4 requires C, 63.15; H, 5.30; N, 5.67%

후처리

  1. additionThe reaction mixture was treated with ultrasound for 0.5 hours
  2. temperatureThe reaction was cooled
  3. additionpoured onto ice
  4. extractionThe mixture was extracted with ethyl acetate (4×100 ml)
  5. extractionThe combined organic extract
  6. extractionwas extracted with 5% sodium bicarbonate solution
  7. extractionthe combined aqueous extract
  8. additionwas poured onto ice
  9. extractionextracted with ethyl acetate
  10. dry with materialThe combined organic extracts were dried (MgSO4)
  11. filtrationfiltered
  12. customevaporated
  13. temperatureheated
  14. customcrystallisation
  15. filtrationFiltration

출처 및 근거

ORD 기록
ord-b6a7a24e5836452aa590d81ae3953bb4
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05334606

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