Hydrochloric Acid → 4-Chlorothieno[2,3-c]pyridine-2-carboxylic acid

HRID 2075332Notes

Reaction equation

HRID 2075332 reaction equation
[Cl:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[S:8][C:9]([C:11]([O:13]C)=[O:12])=[CH:10][C:3]=12.[Li+].[OH-].Cl>C1COCC1>[Cl:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[S:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:3]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 18516294Methyl 4-chlorothieno[2,3-c]pyridine-2-carboxylate

Product 1

HCID 185161084-Chlorothieno[2,3-c]pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-chlorothieno[2,3-c]pyridine-2-carboxylate (19.76 g) was dissolved in 100 mL THF and treated with 100 mL 2M LiOH at room temperature for 3 hours. The reaction mixture was acidified with concentrated HCl to pH=4. A white solid (17.93 g, y=97%) was obtained after filtration, washing with MeOH and air drying. LCMS (API-ES) m/z (%): 214.1 (100%, M++H); 1H NMR (300 MHz, CD3OD) δ ppm 8.35 (s, 1H) 8.71 (s, 1H) 9.54 (s, 1H).

Workup

  1. customA white solid (17.93 g, y=97%) was obtained
  2. filtrationafter filtration
  3. washwashing with MeOH and air
  4. customdrying

Sources & evidence

ORD record
ord-14f2d9fd5fc441b683286fdd102a2376
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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