Sodium Hydroxide → HCID 59463148, compound

HRID 1712927Notes

Reaction equation

HRID 1712927 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][C:9]1[S:13][C:12]([C:14]([O-:16])=[O:15])=[CH:11][CH:10]=1.[OH-].[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][C:9]1[S:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86621559HCID 86621559, compound

Product 1

HCID 59463148HCID 59463148, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-(pyridine-2-ylethynyl)thiophene-2-carboxylate (1.43 g, 5.54 mmol) in ethanol (40 mL) was added sodium hydroxide (0.585 g, 14.6 mmol). The reaction mixture was allowed to stir at rt for 20 h. The solution was concentrated and diluted with 1N aqueous HCl. A precipitate formed and was filtered to give 5-(pyridine-2-ylethynyl)thiophene-2-carboxylic acid (1.02 g, 4.46 mmol) as a yellow solid. LCMS: (FA) ES+ 230.2, ES-229.4.

Workup

  1. concentrationThe solution was concentrated
  2. additiondiluted with 1N aqueous HCl
  3. customA precipitate formed
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-b25333d77bb54d96b53b68c6f51fc0fa
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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