Potassium Carbonate → HCID 67214557, compound

HRID 2421025Notes

Reaction equation

HRID 2421025 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[C:5]([C:8]([OH:10])=[O:9])[C:4]([C:11]([F:14])([F:13])[F:12])=[CH:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24]>CO>[CH3:26][O:25][C:23](=[O:24])[CH2:22][N:7]1[C:2](=[O:1])[CH:3]=[C:4]([C:11]([F:14])([F:12])[F:13])[C:5]([C:8]([OH:10])=[O:9])=[CH:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate2×HCID 27829306-Hydroxy-4-trifluoromethylnicotinic acid

Product 1

HCID 67214557HCID 67214557, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 6-oxo-4-(trifluoromethyl)-1,6-dihydropyridine-3-carboxylic acid (0.207 g) and potassium carbonate (0.553 g) in methanol (5 mL) was added methyl bromoacetate (0.104 mL) at room temperature. After 16 h, the reaction was not complete, so further methyl bromoacetate (0.15 mL) was added. After a further 16 h, the mixture was concentrated in vacuo before the addition of 1 N aqueous hydrochloric acid (30 mL) and extracted into ethyl acetate (3×25 mL), dried over Na2SO4, filtered, and concentrated in vacuo to leave a white solid (300 mg).

Workup

  1. waitAfter a further 16 h
  2. concentrationthe mixture was concentrated in vacuo before the addition of 1 N aqueous hydrochloric acid (30 mL)
  3. extractionextracted into ethyl acetate (3×25 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a641f53777945bda5e2f3c40f785393
Source dataset
uspto-grants-2011_06
Patent number
US07956070B2

Reaction notes

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