HCID 53801930, compound → HCID 18945424, compound

HRID 399812Notes

Reaction equation

HRID 399812 reaction equation
O[N:2]=[CH:3][C:4]1[CH:8]=[CH:7][N:6]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:5]=1>C(OC(=O)C)(=O)C>[C:3]([C:4]1[CH:8]=[CH:7][N:6]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:5]=1)#[N:2]

Participants

3

Reactant 1

HCID 53801930HCID 53801930, compound

Product 1

HCID 18945424HCID 18945424, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

The mixture of methyl 3-(3-hydroxyiminomethylpyrrol-1-yl)benzoate (9.0 g) in acetic anhydride (45 ml) was heated under reflux for 3 hours under stirring and then the reaction mixture was concentrated in vacuo. To the residue was added a mixture of ethyl acetate and water, and the whole was adjusted to pH 8 with potassium carbonate. The separated organic layer was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with chloroform. The eluted fractions containing the desired product were combined and evaporated in vacuo. The residue was triturated with a mixture of diisopropyl ether and n-hexane to give methyl 3-(3-cyanopyrrol-1-yl)benzoate (6.20 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. additionTo the residue was added
  5. additiona mixture of ethyl acetate and water
  6. washThe separated organic layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel eluting with chloroform
  10. additionThe eluted fractions containing the desired product
  11. customevaporated in vacuo
  12. customThe residue was triturated with a mixture of diisopropyl ether and n-hexane

Sources & evidence

ORD record
ord-ec04cfb5eef54edaada16fe4a8ca69fb
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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