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

HRID 2405872Notes

Reaction equation

HRID 2405872 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-971386f63a834f3dac63d58ad3d78e0c
Source dataset
uspto-grants-2014_08
Patent number
US08809327B2

Reaction notes

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