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

HRID 270004Notes

Reaction equation

HRID 270004 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. Rf=0.63 (methylene chloride); (22.2 g; 103 mmol; 85%)

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-38830af035d44438b1b802bd7fffa03e
Source dataset
uspto-grants-2008_11
Patent number
US07449481B2

Reaction notes

Loading…