Water → HCID 12832231, compound

HRID 1447070Notes

Reaction equation

HRID 1447070 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:9][C:10](=[O:17])[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][CH:7]=1.O.Cl.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([S:26](Cl)(=[O:28])=[O:27])[CH:21]=1>C(=O)([O-])[O-].[K+].[K+]>[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([S:26]([NH:1][C:2]2[CH:3]=[C:4]([C:8]3[NH:9][C:10](=[O:17])[C:11](=[CH:15][CH:16]=3)[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][CH:7]=2)(=[O:28])=[O:27])[CH:21]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 12571517Pyridine-3-sulfonyl chloride hydrochloride2×HCID 12832224HCID 12832224, compound

Product 1

HCID 12832231HCID 12832231, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent4×

Procedure

A suspension of 11.5 g (50 mmol) of 6-(3-aminophenyl)-1,2-dihydro-2-oxonicotinic acid and 300 ml of water is stirred at room temperature and 21 g (0.15 mol) of potassium carbonate is added. The solution is cooled to 25° and 13.0 g (61 mmol) of 3-pyridinesulfonyl chloride hydrochloride is slowly added. The solution is clarified by filtration and the pH of the filtrate adjusted to 5.3 with hydrochloric acid. The precipitated solid is filtered, washed with water and dissolved in 300 ml of water containing 10 g (72 mmol) of potassium carbonate. The solution is stirred at room temperature and 10 g (47 mmol) of 3-pyridinesulfonyl chloride hydrochloride is gradually added along with portions of potassium carbonate to maintain a pH of 8. Altogether 10 g (72 mmol) of potassium carbonate is added. The reaction is stirred for 30 min at room temperature and filtered. The pH of the filtrate is adjusted to 6 with hydrochloric acid and the solids filtered and washed with water. A second crop is obtained by lowering the pH of the filtrate to 4.0 and the solid is filtered. The two crops are combined with 200 ml of 1 N sodium hydroxide and heated on the steam bath for 1 hour and filtered. The filtrate is acidified to pH 5.7 with 1 N hydrochloric acid and the solid is filtered, washed with water, methanol, and ether and dried under high vacuum to give 15.2 g of 6-[3-(3-pyridinylsulfonylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid; mp 305° dec.

Workup

  1. temperatureThe solution is cooled to 25°
  2. filtrationThe solution is clarified by filtration
  3. filtrationThe precipitated solid is filtered
  4. washwashed with water
  5. stirringThe solution is stirred at room temperature
  6. temperatureto maintain a pH of 8
  7. stirringThe reaction is stirred for 30 min at room temperature
  8. filtrationfiltered
  9. filtrationthe solids filtered
  10. washwashed with water
  11. customA second crop is obtained
  12. filtrationthe solid is filtered
  13. temperatureheated on the steam bath for 1 hour
  14. filtrationfiltered
  15. filtrationthe solid is filtered
  16. washwashed with water, methanol, and ether
  17. customdried under high vacuum

Sources & evidence

ORD record
ord-4e28475e90184032a8aceed72051e726
Source dataset
uspto-grants-1982_02
Patent number
US04315014

Reaction notes

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