Sodium Hydroxide → 5-(Pyridin-4-yl)thiophene-2-carboxylic acid

HRID 278555Notes

Reaction equation

HRID 278555 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:11][C:10]([C:12]([O:14]C)=[O:13])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[S:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21928559Methyl 5-(pyridin-4-yl)thiophene-2-carboxylate

Product 1

HCID 219285765-(Pyridin-4-yl)thiophene-2-carboxylic acidYield 94.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the obtained methyl 5-(4-pyridyl)-2-thiophenecarboxylate (410 mg) in ethanol (20 ml) was added 1 N sodium hydroxide solution (4 ml) and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated, and the residue was dissolved in water, to which was added 1 N hydrochloric acid (4 ml). The precipitate was filtered, washed with water and dried to give the title compound (363 mg).

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutionthe residue was dissolved in water, to which
  3. additionwas added 1 N hydrochloric acid (4 ml)
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-b3bd37bc43a0402180e8c64f02ce3d2b
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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