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

HRID 2254441Notes

Reaction equation

HRID 2254441 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

Ethyl m-aminobenzoate (1.6 g) was dissolved in 10 ml of glacial acetic acid, and 1.3 g of 2,5-dimethoxytetrahydrofuran was added. The mixture was refluxed for 2 hours, and the solvent was evaporated. The residue was dissolved in a mixture of ethyl acetate and water. The organic layer was separated, and then worked up in a customary manner. Finally, recrystallization from hexane gave 1.7 g (yield 82%) of ethyl 3-(1-pyrrolyl)benzoate as colorless needles having a melting point of 64° to 65° C. The resulting pyrrolyl compound (1.1 g) was dissolved in 30 ml of ethyl ether, and with stirring under ice cooling, 0.2 g of lithium aluminum hydride was added. The mixture was stirred for 1 hour. The reaction mixture was extracted by adding water and ethyl ether. The extract was worked up in a customary manner. Recrystallization from a mixture of ethyl acetate and hexane gave 0.80 g (yield 91%) of 3-(1-pyrrolyl)benzyl alcohol as colorless needles having a melting point of 66° to 68° C.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  4. customThe organic layer was separated
  5. customFinally, recrystallization from hexane

Sources & evidence

ORD record
ord-5c4f32f9e4874c9ab4fcfda8abc07d62
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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