Sodium Hydroxide → Thieno(2,3-b)pyridine-2-carboxylic acid

HRID 1691555Notes

Reaction equation

HRID 1691555 reaction equation
C[O:2][C:3]([C:5]1[S:13][C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1)=[O:4].[OH-].[Na+]>CO.O>[S:13]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[CH:6]=[C:5]1[C:3]([OH:4])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19007380Methyl thieno[2,3-b]pyridine-2-carboxylate

Product 1

HCID 7162095Thieno(2,3-b)pyridine-2-carboxylic acidYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of compound 147-B (0.508 g, 2.63 mmol) in a mixture of MeOH (15 mL) and H2O (3 mL) was added 3N NaOH (1.9 mL, 5.66 mmol) and the reaction mixture was stirred at ambient temperature for 5 h. The solvent was evaporated under reduced pressure, the residue dissolved in H2O, and acidified with 1N HCl. The precipitate was filtered, washed with H2O, and dried under vacuum to afford compound 147-C as a white solid (0.366 g, 78%). MS: m/z 180.0 (MH+).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue dissolved in H2O
  3. filtrationThe precipitate was filtered
  4. washwashed with H2O
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f990995312394c4c8c92e046df7071f9
Source dataset
uspto-grants-2012_04
Patent number
US08153682B2

Reaction notes

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