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

HRID 2254446Notes

Reaction equation

HRID 2254446 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)pyrroleYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.6 g of ethyl m-aminobenzoate was dissolved in 10 ml of glacial acetic acid, and 1.3 g of 2,5-dimethoxytetrahydrofuran was added. The mixture was heated under reflux for 2 hours The solvent was evaporated, and the residue was dissolved in ethyl acetate and water. The organic layer was separated and worked up in a customary manner, and finally recrystallized from hexane to give 1.7 g (yield 82%) of purified ethyl 3-(1-pyrrolyl)-benzoate as colorless needles, m.p. 64°-65° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours The solvent
  3. customwas evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. customThe organic layer was separated
  6. customfinally recrystallized from hexane

Sources & evidence

ORD record
ord-603935b33ece463bb388ed5f3d11ff5f
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

Loading…