Skatole → HCID 13376758, compound

HRID 462505Notes

Reaction equation

HRID 462505 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[H][H].[C:15]1(=[O:20])[O:19][CH2:18][CH2:17][CH2:16]1>CN(C)C=O>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:18][CH2:17][CH2:16][C:15]([OH:20])=[O:19])[CH:3]=1

Participants

6

Reactant 4

HCID 6736SkatoleHCID 7302Gamma-ButyrolactoneHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 13376758HCID 13376758, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methylindole (13.1 g; 1 eq) and sodium hydride (5 g of 50% suspension--1 eq) were melted together in a 3-neck round bottom flask immersed in 100° C. oil bath until evolution of hydrogen gas ceased. The mixture was cooled down and dissolved in 250 mL of dry dimethylformamide. Butyrolactone (17.2 g--2 eq) was added and the solution was refluxed for 7 hr and poured on ice. The mixture was extracted with diethyl ether, and the acid was liberated with 10% hydrochloric acid solution. The mixture was extracted with diethyl ether. Evaporation of the extract gave a residue which was chromatographed on silica gel using 10% (v/v) ethyl acetate in benzene. Evaporation of the appropriate eluates gave 5.5 g of the title compound, mp 82°-84° C.

Workup

  1. customimmersed in 100° C.
  2. temperatureThe mixture was cooled down
  3. temperaturethe solution was refluxed for 7 hr
  4. additionpoured on ice
  5. extractionThe mixture was extracted with diethyl ether
  6. extractionThe mixture was extracted with diethyl ether
  7. customEvaporation of the extract
  8. customgave a residue which
  9. customwas chromatographed on silica gel using 10% (v/v) ethyl acetate in benzene
  10. customEvaporation of the appropriate eluates

Sources & evidence

ORD record
ord-eeee1b80cb22437dac1231eade54af2e
Source dataset
uspto-grants-1985_05
Patent number
US04515949

Reaction notes

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