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

HRID 1779483Notes

Reaction equation

HRID 1779483 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)O1.Cl.ClC1C=CN=CC=1.[C:18]([O:27][CH3:28])(=[O:26])[C:19]1[C:20](=[CH:22][CH:23]=[CH:24][CH:25]=1)[NH2:21]>O1CCOCC1>[N:21]1([C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[C:18]([O:27][CH3:28])=[O:26])[CH:3]=[CH:7][CH:6]=[CH:5]1

Participants

5

Reactant 3

HCID 8635Methyl AnthranilateHCID 790982,5-DimethoxytetrahydrofuranHCID 818524-Chloropyridine hydrochloride

Product 1

HCID 2776733Methyl 2-(1H-pyrrol-1-yl)benzoateYield 92.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

17.14 mol of 2,5-dimethoxytetrahydrofuran and 19.84 g of 4-chloropyridine hydrochloride in 600 ml of 1,4-dioxane are stirred for 10 minutes at 25° C., and then 17.12 mol of methyl anthranilate are added and the suspension is heated at reflux for 3 hours. After removal of the dioxane under reduced pressure, the residue is taken up in 1 liter of water and extracted with diethyl ether. The ethereal phase is washed with water, decanted off, dried over magnesium sulfate, rendered colourless with animal charcoal, and then concentrated under reduced pressure to yield the title product in the form of an oil.

Workup

  1. temperaturethe suspension is heated
  2. temperatureat reflux for 3 hours
  3. customAfter removal of the dioxane under reduced pressure
  4. extractionextracted with diethyl ether
  5. washThe ethereal phase is washed with water
  6. customdecanted off
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3a474b3b509f45d78e4956e88494e5e4
Source dataset
uspto-grants-1997_05
Patent number
US05627203

Reaction notes

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