Anthranilic Acid → 2-(4-Pyridylamino)benzoic acid

HRID 64882Notes

Reaction equation

HRID 64882 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].Cl.Cl[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[N:16]1[CH:17]=[CH:18][C:13]([NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:10])=[O:9])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 818524-Chloropyridine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 4101332-(4-Pyridylamino)benzoic acidYield 99.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 274.5 g (2.0 moles) of anthranilic acid, 300 g (2.0 moles) of 4-chloropyridine hydrochloride and 180 g (2.19 moles) of anhydrous sodium acetate in 855 ml of glacial acetic acid was stirred at reflux for three hours. The mixture was cooled to room temperature and the precipitated solid was filtered. The product was washed with a small amount of cold acetic acid followed by cold ether. It was dried at 75° C., in vacuo to give 428 g (85.6%) of 2-(4-pyridinylamino)benzoic acid as the hydrochloride salt, m.p. 275°-280° C.(decompn.).

Workup

  1. temperatureat reflux for three hours
  2. filtrationthe precipitated solid was filtered
  3. washThe product was washed with a small amount of cold acetic acid
  4. customIt was dried at 75° C., in vacuo

Sources & evidence

ORD record
ord-9ab274559aec4721905c12d34dea2966
Source dataset
uspto-grants-1986_09
Patent number
US04610991

Reaction notes

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