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

HRID 1072998Notes

Reaction equation

HRID 1072998 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 H2O (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 H2O (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 H2O (12 mL)
  3. customThe precipitated solid is removed by filtration
  4. washthe solid is rinsed with ether

Sources & evidence

ORD record
ord-3d7ca39a987b4f4da4979de538c8eb14
Source dataset
uspto-grants-2005_06
Patent number
US06911543B2

Reaction notes

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