Sodium Hydroxide → Thieno[3,2-b]pyridine-5-carboxylic acid

HRID 1492414Notes

Reaction equation

HRID 1492414 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=O.[OH-].[Na+].[C:11]([O-:16])(=[O:15])[C:12]([CH3:14])=O.[Na+]>CCO>[S:4]1[C:3]2[C:2](=[N:1][C:12]([C:11]([OH:16])=[O:15])=[CH:14][CH:7]=2)[CH:6]=[CH:5]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 8188673-aminothiophene-2-carbaldehydeHCID 23662274Sodium pyruvate

Product 1

HCID 12210216Thieno[3,2-b]pyridine-5-carboxylic acidYield 71.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-amino-2-formylthiophene (10 g, 78 mmol) in EtOH (50 mL) was added a mixture of aqueous NaOH (50 mL, 5%) and sodium pyruvate (17.16 g, 156 mmol). The mixture was heated to 60° C. for 2 hr. The mixture was cooled and washed with Et2O: EtOAc 1:1 and then acidified with 1 N HCl to pH 3 at 0° C. The mixture was filtered and the solid was air dried to give 10 g (71%) of the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with Et2O: EtOAc 1:1
  3. customacidified with 1 N HCl to pH 3 at 0° C
  4. filtrationThe mixture was filtered
  5. customdried

Sources & evidence

ORD record
ord-f735fc85b2044fddaed3c6a4eaefd8c1
Source dataset
uspto-grants-1994_12
Patent number
US05374635

Reaction notes

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