Hydrochloric Acid → 7-CHLOROTHIENO[3,2-B]PYRIDINE-6-CARBOXYLIC ACID

HRID 1611484Notes

Reaction equation

HRID 1611484 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][N:5]=[C:4]2[CH:13]=[CH:14][S:15][C:3]=12.Cl>C(O)C.[OH-].[Na+]>[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[C:4]2[CH:13]=[CH:14][S:15][C:3]=12

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15565869Ethyl 7-chlorothieno[3,2-b]pyridine-6-carboxylate

Product 1

HCID 112873397-CHLOROTHIENO[3,2-B]PYRIDINE-6-CARBOXYLIC ACIDYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of ethyl 7-chlorothieno[3,2-b]pyridine-6-carboxylate (2.98 g, 12.3 mmol) [Thompson, M.; Forbes, I. F. EP 126970] in 40 mL of ethanol and 15 mL of 2.5 N sodium hydroxide is heated at reflux for 1 hour. The mixture is cooled to 0° C. and the pH is adjusted to 4 by the addition of 4 N hydrochloric acid. The mixture is stirred at room temperature and the resulting precipitate is collected by filtration washing with water to provide 2.47 g of 7-chlorothieno[3,2-b]pyridine-6-carboxylic acid as a white solid, 1H NMR (DMSO-d6) δ 7.73 (d, J=6 Hz, 1H), 8.44 (d, J=6 Hz, 1H), 9.07 (s, 1H).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. filtrationthe resulting precipitate is collected by filtration
  4. washwashing with water

Sources & evidence

ORD record
ord-6481784d6d28441385aef626058cc9b9
Source dataset
uspto-grants-2006_01
Patent number
US06987116B2

Reaction notes

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