Sodium Hydroxide → HCID 19700938, compound

HRID 1081337Notes

Reaction equation

HRID 1081337 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[C:9]([C:14]([OH:16])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=2)=[O:7])=[CH:4][CH:3]=1.[OH-:19].[Na+].[O-:21][Mn](=O)(=O)=O.[K+]>C(O)(C)C>[C:1]([C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[C:9]([C:14]([OH:16])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=2)=[O:7])=[CH:17][CH:18]=1)([OH:21])=[O:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 103319012-Pyridinecarboxylic acid, 3-(4-methylbenzoyl)-

Product 1

HCID 19700938HCID 19700938, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 3-(4-methylbenzoyl)-2-pyridinecarboxylic acid (6.0 g) and 0.1N-NaOH (340 ml) was added portionwise KMnO4 (8.0 g), while stirring at room temperature. After this mixture was heated at 90°-100° C. for 1.5 hour, isopropanol was added to the mixture, and the resulting precipitate was filtered off. To the filtrate was added c.HCl to adjust the pH 2. The solution was saturated with NaCl and extracted with ethyl acetate-THF (about 3:1). The extract was washed with ag. NaCl, dried, and the solvent was evaporated to give 3-(4-carboxybenzoyl)-2-pyridinecarboxylic acid as colorless crystals (1.50 g).

Workup

  1. temperatureAfter this mixture was heated at 90°-100° C. for 1.5 hour
  2. filtrationthe resulting precipitate was filtered off
  3. additionTo the filtrate was added c
  4. extractionextracted with ethyl acetate-THF (about 3:1)
  5. washThe extract was washed with ag
  6. dry with materialNaCl, dried
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-58e220bb7d9a4567b94948dd5117bb40
Source dataset
uspto-grants-1996_12
Patent number
US05585385

Reaction notes

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