Hydrochloric Acid → HCID 10263984, compound

HRID 1741665Notes

Reaction equation

HRID 1741665 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 10263984HCID 10263984, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Conditions

Temperature
145 °C

Procedure

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%

Workup

  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

Sources & evidence

ORD record
ord-b6a7a24e5836452aa590d81ae3953bb4
Source dataset
uspto-grants-1994_08
Patent number
US05334606

Reaction notes

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