Hydrochloric Acid → HCID 69023699, compound

HRID 1865078Notes

Reaction equation

HRID 1865078 reaction equation
[OH:1]O.[Se](=O)=O.[CH2:6]([O:8][C:9]([C:11]1[N:12]([CH3:28])[C:13]([CH2:26][CH3:27])=[C:14]([C:24]#[N:25])[C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[O:23])=[CH:18][CH:17]=1)=[O:10])[CH3:7].Cl>>[CH2:6]([O:8][C:9]([C:11]1[N:12]([CH3:28])[C:13]([CH2:26][CH3:27])=[C:14]([C:24]#[N:25])[C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([OH:1])=[O:23])=[CH:18][CH:17]=1)=[O:10])[CH3:7]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 24007Selenium DioxideHCID 86611444HCID 86611444, compound

Product 1

HCID 69023699HCID 69023699, compound

Procedure

Add 30% hydrogen peroxide (0.66 mL, 5.8 mmol) and selenium dioxide (0.016 g, 0.15 mmol) to 4-cyano-5-ethyl-3-(4-formyl-phenyl)-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (prepared in example E-152), and heat to reflux with stirring. After 18 hours, cool the reaction mixture and pour into 1N HCl. Extract the quenched reaction with methylene chloride. Combine the organic extracts, wash with water and brine, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Recrystallize the residue from ethyl acetate:hexanes to provide the title compound. Mass spectrum (m/e): 325.1 (M−1).

Workup

  1. temperatureheat
  2. temperatureto reflux
  3. temperaturecool the reaction mixture
  4. extractionExtract
  5. customthe quenched reaction with methylene chloride
  6. washwash with water and brine
  7. dry with materialdry over anhydrous magnesium sulfate
  8. filtrationfilter
  9. concentrationconcentrate under reduced pressure
  10. customRecrystallize the residue from ethyl acetate

Sources & evidence

ORD record
ord-2a3efcbeb7464151a8d5fc8d57e256ab
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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