Methyl Anthranilate → Methyl 2-(1H-pyrrol-1-yl)benzoate

HRID 845380Notes

Reaction equation

HRID 845380 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].CO[CH:14]1[CH2:18][CH2:17][CH:16](OC)O1>C(O)(=O)C>[N:4]1([C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([O:10][CH3:11])=[O:9])[CH:14]=[CH:18][CH:17]=[CH:16]1

Participants

4

Reactant 2

HCID 8635Methyl AnthranilateHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 2776733Methyl 2-(1H-pyrrol-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 500 g of methyl anthranilate and 438 g of 2,5-dimethoxytetrahydrofuran in 670 ml of glacial acetic acid is heated at reflux temperature for 11/2 hours. The acetic acid is then evaporated under reduced pressure and the residue is distilled to yield methyl 2-(1H-pyrrol-1-yl)-benzoate, b.p. 109°/0.1 mm Hg.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 11/2 hours
  3. customThe acetic acid is then evaporated under reduced pressure
  4. distillationthe residue is distilled

Sources & evidence

ORD record
ord-0bfb77e6bc12409ebf3689e5c4715367
Source dataset
uspto-grants-1988_07
Patent number
US04758559

Reaction notes

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