2-Amino-4-chlorobenzoic acid → 5-chloro-2-(1H-pyrrol-1-yl)benzoic acid

HRID 1779482Notes

Reaction equation

HRID 1779482 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5]([O:8]C)[O:4]1.Cl.Cl[C:12]1[CH:17]=[CH:16][N:15]=[CH:14]C=1.NC1[CH:27]=[C:26]([Cl:28])[CH:25]=CC=1C(O)=O>O1CCOCC1>[Cl:28][C:26]1[CH:25]=[CH:3][C:7]([N:15]2[CH:14]=[CH:12][CH:17]=[CH:16]2)=[C:6]([CH:27]=1)[C:5]([OH:8])=[O:4]

Participants

5

Reactant 3

HCID 666462-Amino-4-chlorobenzoic acidHCID 790982,5-DimethoxytetrahydrofuranHCID 818524-Chloropyridine hydrochloride

Product 1

HCID 121961975-chloro-2-(1H-pyrrol-1-yl)benzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

18.6 ml (0.143 mol) of 2,5-dimethoxytetrahydrofuran are stirred for 10 minutes with 21.5 g (0.143 mol) of 4-chloropyridine hydrochloride in 600 ml of 1,4-dioxane. 24.6 g (0.143 mol) of 2-amino-4-chlorobenzoic acid are added, and the mixture is heated at reflux for 4 hours. After removal of the dioxane under reduced pressure, the residue is taken up with 1 liter of water and extracted with 800 ml of diethyl ether. The ethereal phase is washed with water and then extracted with 500 ml of a saturated aqueous sodium hydrogen carbonate solution. The aqueous phase is acidified with 10N hydrochloric acid and then extracted with 800 ml of diethyl ether. The ethereal phase is washed with water, decanted off, dried over magnesium sulfate, rendered colourless with animal charcoal and concentrated under reduced pressure to yield the title compound in the form of a grey powder.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 4 hours
  3. customAfter removal of the dioxane under reduced pressure
  4. extractionextracted with 800 ml of diethyl ether
  5. washThe ethereal phase is washed with water
  6. extractionextracted with 500 ml of a saturated aqueous sodium hydrogen carbonate solution
  7. extractionextracted with 800 ml of diethyl ether
  8. washThe ethereal phase is washed with water
  9. customdecanted off
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-abc919d14eb64347ad6c36ac3a00dabd
Source dataset
uspto-grants-1997_05
Patent number
US05627203

Reaction notes

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