2-Methoxyethanol → HCID 57475690, compound

HRID 719941Notes

Reaction equation

HRID 719941 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10]C)=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][CH2:20][CH2:21][OH:22]>O>[CH3:18][O:19][CH2:20][CH2:21][O:22][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 11430Potassium CarbonateHCID 406081Methyl 5-chloropyrazine-2-carboxylate

Product 1

HCID 57475690HCID 57475690, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A solution of methyl 5-chloropyrazine-2-carboxylate (2.0 g, 11.63 mmol) in 2-methoxyethanol (20 mL) was treated with solid potassium carbonate (4.8 g, 34.8 mmol). The mixture was heated at 95° C. and was stirred at this temperature for 4.5 h. The mixture was dissolved in water (20 mL) and extracted with diethyl ether. The aqueous layer was neutralized with a 1N aqueous hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo to afford 5-methoxyethoxypyrazine-2-carboxylic acid as a pale yellow solid powder: (1.89 g, 82.2%).

Workup

  1. extractionextracted with diethyl ether
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9db3ed1fb1f642f9ba9c3e8c63ac01c9
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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