2,5-Dichlorobenzoic acid → HCID 23337819, compound

HRID 903146Notes

Reaction equation

HRID 903146 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(O)CCCC.C(=O)([O-])[O-].[K+].[K+].[NH2:24][C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[N:29][CH:30]=1>[Cu]=O>[Cl:11][C:8]1[CH:9]=[CH:10][C:2]([NH:24][C:25]2[CH:30]=[N:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 57842,5-Dichlorobenzoic acidHCID 62761-PentanolHCID 11430Potassium CarbonateHCID 811216-Methoxy-3-pyridinylamine

Product 1

HCID 23337819HCID 23337819, compound

Reagents, catalysts & solvents 1

HCID 14829Copper oxideCatalyst

Conditions

Temperature
100 °C

Procedure

To a solution of 19.1 g. of 2,5-dichlorobenzoic acid [Besley & Goldberg, J. Chem. Soc., 2448 (1954)] in 100 ml. of amyl alcohol is added 6.9 g. of anhydrous potassium carbonate and 0.1 g. of copper oxide. The mixture is stirred and heated at 100° C. for 30 minutes, then 13.0 g. of 5-amino-2-methoxypyridine is added and the mixture is heated at reflux and stirred for 3 hours. A small amount of water forms and is collected in a Dean-Stark apparatus. The reaction mixture is cooled, poured into water and made basic with potassium carbonate. The mixture is steam-distilled to remove the amyl alcohol, then filtered and the filtrate is acidified to pH 6. The mixture is again filtered and this pink filtrate is acidified with 6 N hydrochloric acid to pH 4. The solid is collected, giving 5-chloro-2-(6-methoxy-3-pyridylamino)benzoic acid as a pink crystalline solid.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux
  3. stirringstirred for 3 hours
  4. customA small amount of water forms and is collected in a Dean-Stark apparatus
  5. temperatureThe reaction mixture is cooled
  6. additionpoured into water
  7. distillationThe mixture is steam-distilled
  8. customto remove the amyl alcohol
  9. filtrationfiltered
  10. filtrationThe mixture is again filtered
  11. customThe solid is collected

Sources & evidence

ORD record
ord-5896734082744c038f4d70bd695551ad
Source dataset
uspto-grants-1980_10
Patent number
US04226869

Reaction notes

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