Ethyl 3-aminobenzoate → 1-(3-Ethoxycarbonylphenyl)pyrrole

HRID 1759201Notes

Reaction equation

HRID 1759201 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].CO[CH:15]1[CH2:19][CH2:18][CH:17](OC)O1>C(O)(=O)C>[N:1]1([C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:15]=[CH:19][CH:18]=[CH:17]1

Participants

4

Reactant 2

HCID 11400Ethyl 3-aminobenzoateHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 47637241-(3-Ethoxycarbonylphenyl)pyrrole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 60 ml of stirred glacial acetic acid was added 25.0 grams (0.15 mole) of ethyl 3-aminobenzoate. The mixture was stirred for two minutes and 19.6 grams (0.15 mole) of 2,5-dimethoxytetrahydrofuran was added during a five minute period. Upon complete addition the red solution was heated under reflux for 1.5 hours. The acetic acid solvent was removed by distillation. Higher boiling volatiles were also removed by distillation, under reduced pressure (80°-110° C./55 2 mm). Pure ethyl 3-(pyrrol-1-yl)benzoate was obtained by distillation under reduced pressure; bp 143°-145° C./2 mm. The product solidified on standing; mp 62°-64° C. The yield was 25.4 grams of white solid.

Workup

  1. additionUpon complete addition the red solution
  2. temperaturewas heated
  3. temperatureunder reflux for 1.5 hours
  4. customThe acetic acid solvent was removed by distillation
  5. customHigher boiling volatiles were also removed by distillation, under reduced pressure (80°-110° C./55 2 mm)

Sources & evidence

ORD record
ord-b1d6e457c9684dc885feacb461893753
Source dataset
uspto-grants-1982_07
Patent number
US04339457

Reaction notes

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