Methanol → Methyl pyrazinoate

HRID 7163

Reaction equation

HRID 7163 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=[O:8].OS(O)(=O)=O.[CH3:15]O>>[CH3:15][O:8][C:7]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 10472-Pyrazinecarboxylic acidHCID 1118Sulfuric Acid

Product 1

HCID 72662Methyl pyrazinoateYield 59%

Procedure

A solution of 2-pyrazinecarboxylic acid (2.00 g, 16.1 mmol) and H2SO4 (catalytic) in MeOH (50 mL) was heated at reflux for 45 minutes, then concentrated in vacuo. The residue was partitioned between EtOAc (40 mL) and saturated NaHCO3(aq) (20 mL). The organic phase was washed with saturated NaHCO3(aq) (20 mL) and brine (10 mL), then dried (MgSO4) and concentrated in vacuo to give colourless crystals (1.32 g, 59%). 1H NMR (CDCl3) □ 4.04 (s, 3H), 8.72 (dd, 11H, J=2.4, 1.2 Hz), 8.77 (d, 1H, J=2.4 Hz), 9.32 (d, 1H, J=1.2 Hz).

Workup

  1. temperatureat reflux for 45 minutes
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between EtOAc (40 mL) and saturated NaHCO3(aq) (20 mL)
  4. washThe organic phase was washed with saturated NaHCO3(aq) (20 mL) and brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1245e15db51147829497f5c1ab0ba500
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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