Sodium Hydroxide → Thieno[3,2-c]pyridine-6-carboxylic acid

HRID 1830548Notes

Reaction equation

HRID 1830548 reaction equation
[S:1]1[C:9]2[CH:8]=[C:7]([C:10]([O:12]C)=[O:11])[N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.[OH-].[Na+]>CO.O>[S:1]1[C:9]2[CH:8]=[C:7]([C:10]([OH:12])=[O:11])[N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10954414Thieno[3,2-c]pyridine-6-carboxylic acid, methyl ester

Product 1

HCID 12277676Thieno[3,2-c]pyridine-6-carboxylic acidYield 43%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl thieno[3,2-c]pyridine-6-carboxylate (C155) (678 mg, 3.5 mmol) is dissolved in MeOH (16 mL) and water (2 mL). 2M NaOH (1.8 mL, 3.6 mmol) is added drop-wise, and the solution stirred at rt. After 2 days (complete disappearance of ester by TLC), the solution is concentrated in vacuo. The residue is dissolved in water (12 mL), and the pH is adjusted to 3.5 with 10% HCl. The precipitated solid is removed by filtration, and the solid is rinsed with ether, affording thieno[3,2-c]pyridine-6-carboxylic acid (C160) as a white solid (43% yield). HRMS (FAB) calculated for C8H5NO2S+H: 180.0119, found 180.0123 (M+H)+.

Workup

  1. concentrationthe solution is concentrated in vacuo
  2. dissolutionThe residue is dissolved in water (12 mL)
  3. customThe precipitated solid is removed by filtration
  4. washthe solid is rinsed with ether

Sources & evidence

ORD record
ord-2a0b3d81e6604bc88da07f45f1e395b5
Source dataset
uspto-grants-2006_06
Patent number
US07067515B2

Reaction notes

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