3-Pyridineacetic acid → HCID 20251890, compound

HRID 1284489Notes

Reaction equation

HRID 1284489 reaction equation
[NH:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][C:22](O)=O)[CH:16]=1.P(Cl)(Cl)(Cl)=O>C(Cl)(Cl)Cl>[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][C:22]2[N:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[N:10]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 1083-Pyridineacetic acidHCID 24813Phosphorus oxychlorideHCID 68297N-Phenyl-o-phenylenediamine

Product 1

HCID 20251890HCID 20251890, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-anilinoaniline (1.84 g) and 3-pyridineacetic acid (1.37 g) in chloroform (20 ml) was dropwise added phosphorus oxychloride (1.53 g) and the mixture was refluxed for 6 hours. After removal of the solvent under reduced pressure, the resultant residue was poured into a saturated aqueous solution of sodium bicarbonate. The mixture was extracted twice with ethyl acetate. The combined extract was washed with water and a saturated aqueous solution of sodium chloride successively, and dried over magnesium sulfate. The solvent was removed under reduced pressure to give a crystalline product, which was recrystallized from a mixture of isopropyl alcohol and n-hexane (1:2) to give 2-(pyridin-3-yl)methyl-1-phenyl-1H-benzimidazole (1.0 g).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customAfter removal of the solvent under reduced pressure
  3. additionthe resultant residue was poured into a saturated aqueous solution of sodium bicarbonate
  4. extractionThe mixture was extracted twice with ethyl acetate
  5. extractionThe combined extract
  6. washwas washed with water
  7. dry with materiala saturated aqueous solution of sodium chloride successively, and dried over magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customto give a crystalline product, which
  10. customwas recrystallized from a mixture of isopropyl alcohol and n-hexane (1:2)

Sources & evidence

ORD record
ord-4c85aafd021f45bbba2efd3a13f3b7e1
Source dataset
uspto-grants-1986_01
Patent number
US04563455

Reaction notes

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