Sodium Hydroxide → HCID 58374131, compound

HRID 1948551Notes

Reaction equation

HRID 1948551 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]([O:18]CC)=[O:17])[N:9]=[CH:8]1.[OH-].[Na+]>CCO.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]([C:12]([F:13])([F:14])[F:15])=[C:10]([C:16]([OH:18])=[O:17])[N:9]=[CH:8]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58374107HCID 58374107, compound

Product 1

HCID 58374131HCID 58374131, compoundYield 12.94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-imidazole-4-carboxylate (1.2 g, 4.21 mmol) in EtOH (20 mL) was added a predissolved solution of sodium hydroxide (1.00 g, 25.1 mmol) in water (5.00 mL). The reaction mixture was stirred overnight at room temperature. The next day, the reaction mixture was concentrated in vacuo, acidified with dilute HCl, and extracted from 1 M HCl with EtOAc. Some product did extract but the aqueous layer remained yellow with desired product as well. The aqueous layer was brought to pH 5 using ammonium hydroxide and NH4Cl and extracted with EtOAc again which afforded additional product. The combined organic layers were dried over MgSO4, filtered, concentrated to give 1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-imidazole-4-carboxylic acid (140 mg, 0.544 mmol, 12.94% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.5 (1H, br s), 8.69 (1H, dd), 8.35 (s, 1H), 8.14 (1H, dt), 7.78 (1H, d), 7.67 (1H, dt).

Workup

  1. concentrationThe next day, the reaction mixture was concentrated in vacuo
  2. extractionextracted from 1 M HCl with EtOAc
  3. extractionSome product did extract
  4. extractionextracted with EtOAc again which
  5. customafforded additional product
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-46da93a1beb6492baab419ab3ef4ca97
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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