Benzoic acid, 3-amino-, methyl ester → Methyl 3-(1H-pyrrol-1-yl)benzoate

HRID 399862Notes

Reaction equation

HRID 399862 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].CO[CH:14]1[CH2:18][CH2:17][CH:16](OC)O1>C(O)(=O)C>[N:1]1([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH:14]=[CH:18][CH:17]=[CH:16]1

Participants

4

Reactant 2

HCID 78274Benzoic acid, 3-amino-, methyl esterHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 3322314Methyl 3-(1H-pyrrol-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The mixture of methyl 3-aminobenzoate (110.0 g) and 2,5-dimethoxytetrahydrofuran (141.4 ml) in acetic acid (330 ml) was heated under reflux for 50 minutes under stirring and the solvent was removed by concentration in vacuo. To the residue was added a mixture of ethyl acetate and water, and adjusted to pH 8 with potassium carbonate. The separated organic layer was washed with water and dried over magnesium sulfate. Evaporation of a solvent gave a residue, which was purified by column chromatography on silica gel eluting with chloroform. The eluted fractions containing the desired product were collected and evaporated in vacuo to give methyl 3-(pyrrol-1-yl)benzoate (112.84 g) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 50 minutes
  3. customthe solvent was removed by concentration 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. customEvaporation of a solvent
  9. customgave a residue, which
  10. customwas purified by column chromatography on silica gel eluting with chloroform
  11. additionThe eluted fractions containing the desired product
  12. customwere collected
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-fda32e49985d4330911b762f0da88c8e
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

Loading…