ChemicalBook CAS DataBase List Thieno[2,3-c]pyridine-2-carboxylic acid (9CI)

Thieno[2,3-c]pyridine-2-carboxylic acid (9CI) synthesis

4synthesis methods

Product Name:Thieno[2,3-c]pyridine-2-carboxylic acid (9CI)
CAS Number:478149-00-7
Molecular formula:C8H5NO2S
Molecular Weight:179.2

ethyl thieno[2,3-c]pyridine-2-carboxylate

478148-99-1

Thieno[2,3-c]pyridine-2-carboxylic acid (9CI)

478149-00-7

Ethyl thieno[2,3-c]pyridine-2-carboxylate (C121, 577 mg, 2.99 mmol) was added to a solvent mixture of methanol (15 mL) and water (1.5 mL) with 2 M sodium hydroxide solution (1.5 mL, 3.0 mmol). The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, the solvent was removed by vacuum concentration and the residue was dissolved in water (75 mL). The solution was acidified to pH 3 with concentrated hydrochloric acid to form a slurry. The solid product was collected by filtration, washed sequentially with water and ether, and dried to give thieno[2,3-c]pyridine-2-carboxylic acid (C122) as an off-white solid in 38% yield. High-resolution mass spectrometry (FAB) analysis showed that the calculated value of C8H5NO2S + H was 180.0119 and the measured value was 180.0119 (M + H)+.

478148-99-1
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478149-00-7
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Yield:478149-00-7 38%

Reaction Conditions:

with sodium hydroxide in methanol;water;

Steps:

17 Preparation of the Acid:

C121 (577 mg, 2.99 mmol) is combined with 2M NaOH (1.5 mL, 3.0 mmol) in MeOH (15 mL) and H₂O (1.5 mL). The reaction is stirred at rt for 24 h. The reaction is concentrated in vacuo and the residue is dissolved in water (75 mL). Concentrated HCl is used to acidify the solution to pH 3. The slurry is filtered, washed with H₂O and ether, and dried, affording thieno[2,3-c]pyridine-2-carboxylic acid (C122) as an off-white solid (38% yield). HRMS (FAB) calculated for C₈H₅NO₂S+H: 180.0119, found 180.0119 (M+H)⁺.

References:

US2003/45540,2003,A1

625-92-3 Synthesis