Sodium Hydroxide → Benzoic acid, 4-((3-pyridinylcarbonyl)amino)-

HRID 1957598Notes

Reaction equation

HRID 1957598 reaction equation
C([C:3]1[CH:11]=[C:10]([NH:12][C:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:14])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])C.[OH-].[Na+]>CO>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:13]([NH:12][C:10]2[CH:11]=[CH:3][C:4]([C:5]([OH:7])=[O:6])=[CH:8][CH:9]=2)=[O:14])[CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54452435HCID 54452435, compound

Product 1

HCID 79836Benzoic acid, 4-((3-pyridinylcarbonyl)amino)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 12.0 g (0.044 mol) of ethyl 4-[(3-pyridinylcarbonyl)amino]benzoic acid, 65 ml of 2N sodium hydroxide and 120 ml of methanol is refluxed for 0.75 hour. The solvent is removed and the residue extracted with diethyl ether. The residue is diluted with water and solid citric acid is added until the pH is 4-5. The mixture is filtered and the solid washed with water and air dried to give crystals, m.p. 307°-310° C.

Workup

  1. temperatureis refluxed for 0.75 hour
  2. customThe solvent is removed
  3. extractionthe residue extracted with diethyl ether
  4. additionThe residue is diluted with water and solid citric acid
  5. additionis added until the pH is 4-5
  6. filtrationThe mixture is filtered
  7. washthe solid washed with water and air
  8. customdried
  9. customto give crystals, m.p. 307°-310° C.

Sources & evidence

ORD record
ord-5211e189b0a444fba3c9d5b97fffa613
Source dataset
uspto-grants-1998_07
Patent number
US05786353

Reaction notes

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