Potassium Hydroxide → 1286756-62-4

HRID 1526587Notes

Reaction equation

HRID 1526587 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:11]([O:13]CC)=[O:12])=[N:5][CH:6]=[C:7]([O:9][CH3:10])[N:8]=1.[OH-].[K+]>CO>[CH3:1][O:2][C:3]1[C:4]([C:11]([OH:13])=[O:12])=[N:5][CH:6]=[C:7]([O:9][CH3:10])[N:8]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86715868HCID 86715868, compound

Product 1

HCID 681113251286756-62-4Yield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 3,5-dimethoxypyrazine-2-carboxylate (0.314 g, 1.48 mmol) in MeOH (5 mL) at room temperature was added potassium hydroxide (0.135 g, 2.41 mmol). The reaction mixture was stirred at RT for 17 h, quenched with 5 M HCl (0.48 mL), and diluted with EtOAc. The solid was removed by filtration and the filtrate was concentrated. Purification by flash column chromatography on silica gel (10% MeOH in DCM) gave 3,5-dimethoxypyrazine-2-carboxylic acid (0.261 g, 1.42 mmol, 96% yield) as a white solid. LC/MS (ESI+) m/z=185.1 (M+H)+.

Workup

  1. customquenched with 5 M HCl (0.48 mL)
  2. additiondiluted with EtOAc
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customPurification by flash column chromatography on silica gel (10% MeOH in DCM)

Sources & evidence

ORD record
ord-1e0c4294ba4c4b32b9d7879d4a416d4d
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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