Ethanol → Ethyl 5-methylpyrazine-2-carboxylate

HRID 1867005Notes

Reaction equation

HRID 1867005 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[CH2:11](O)[CH3:12]>>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 702EthanolHCID 1228315-Methyl-2-pyrazinecarboxylic acid

Product 1

HCID 16114819Ethyl 5-methylpyrazine-2-carboxylateYield 67%

Procedure

A solution of 5-methylpyrazine-2-carboxylic acid (15.0 g, 0.109 mol) in ethanol (70.0 mL) containing (1.5 g, 0.0079 mol) was heated to reflux for 4 h under argon atmosphere. The dark colored solution was cooled, added sod.bicarbonate (1.0 g) and concentrated under reduced pressure. The residue was partitioned between water (50 mL) and EtOAc (100 mL). The organic layer was washed with water (2×25 mL), dried (Na2SO4), and concentrated under reduced pressure to afford ethyl 5-methylpyrazine-2-carboxylate (12.05 g, 67%) as an orange colored liquid: 1H NMR (CD3OD/400 MHz) δ9.1 (d. 1H, J=1.2 Hz), 8.62 (d, 1H, J=1.2 Hz), 4.45 (q, 2H, J=7.2 Hz), 2.63 (s, 3H), and 1.41 (t, 3H, J=7.2 Hz); ESMS m/z 167 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h under argon atmosphere
  3. temperatureThe dark colored solution was cooled
  4. additionadded sod
  5. concentrationbicarbonate (1.0 g) and concentrated under reduced pressure
  6. customThe residue was partitioned between water (50 mL) and EtOAc (100 mL)
  7. washThe organic layer was washed with water (2×25 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e99c41c4dc7d4d2e9e7ff9ddfd658b01
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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