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

HRID 2293180Notes

Reaction equation

HRID 2293180 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-1625e8102b4a4a4ba93b2856599e4547
Source dataset
uspto-grants-1997_11
Patent number
US05686445

Reaction notes

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