Acetic Anhydride → HCID 15010120, compound

HRID 248395Notes

Reaction equation

HRID 248395 reaction equation
[CH:1]([NH:3][CH:4]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:5](O)=O)=O.ClC(=C)[C:17]#[N:18].[C:20](OC(=O)C)(=O)C>>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([C:4]2[NH:3][CH:1]=[CH:20][C:5]=2[C:17]#[N:18])=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 701982-ChloroacrylonitrileHCID 19759558HCID 19759558, compound

Product 1

HCID 15010120HCID 15010120, compound

Conditions

Temperature
90 °C

Procedure

To a stirred suspension of 2-formylamino-2-(4-methylphenyl)acetic acid (4.00 g) in acetic anhydride (45 ml) was added 2-chloroacrylonitrile (16.5 ml) at room temperature and the resulting suspension was heated at 90° C. for 2.5 hours. After cooling, the solvent was evaporated and the residue was washed with isopropyl ether. The mixture was filtered and the resulting solid was dissolved into ethyl acetate and the solution was washed with aqueous saturated sodium bicarbonate and water successively. The organic layer was dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with n-hexane/methylene chloride 1:3 (V/V) to give 2-(4-methylphenyl)pyrrole-3-carbonitrile (0.73 g) as a colorless viscous oil.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated
  3. washthe residue was washed with isopropyl ether
  4. filtrationThe mixture was filtered
  5. dissolutionthe resulting solid was dissolved into ethyl acetate
  6. washthe solution was washed with aqueous saturated sodium bicarbonate and water successively
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel column chromatography
  11. washeluted with n-hexane/methylene chloride 1:3 (V/V)

Sources & evidence

ORD record
ord-cdc18fd29b404a3d9ff823c6d2be1cd1
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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