Ethyl 2-aminobenzoate → Ethyl 2-(1H-pyrrol-1-yl)benzoate

HRID 1013145Notes

Reaction equation

HRID 1013145 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11])[CH3:2].CO[CH:15]1[CH2:19][CH2:18][CH:17](OC)O1>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH:15]=[CH:19][CH:18]=[CH:17]1)[CH3:2]

Participants

4

Reactant 2

HCID 6877Ethyl 2-aminobenzoateHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 12673310Ethyl 2-(1H-pyrrol-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 2-amino benzoic acid ethyl ester (20 g; 121 mmol) in acetic acid (35 mL) was added 2,5-dimethoxytetrahydrofuran (19 g; 174 mmol). The reaction mixture was stirred for two hours at reflux. After evaporation of the solvent, the crude product was purified by flash column chromatography (methylene chloride) to give compound 2-pyrrol-1-yl-benzoic acid ethyl ester as a yellow oil.

Workup

  1. temperatureat reflux
  2. customAfter evaporation of the solvent
  3. customthe crude product was purified by flash column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-13351d2d816642799b830ec75ccde29a
Source dataset
uspto-grants-2011_07
Patent number
US07981907B2

Reaction notes

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