Water → 5-Ethoxypyrazine-2-carboxylic acid

HRID 2045855Notes

Reaction equation

HRID 2045855 reaction equation
[CH2:1]([O:3][C:4]1[N:5]=[CH:6][C:7]([C:10]([O:12]CC)=[O:11])=[N:8][CH:9]=1)[CH3:2].O.O.[OH-].[Li+].C([O-])(O)=O.[Na+]>O1CCOCC1.CCOCC>[CH2:1]([O:3][C:4]1[N:5]=[CH:6][C:7]([C:10]([OH:12])=[O:11])=[N:8][CH:9]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 516892Sodium BicarbonateHCID 668696851262803-60-0

Product 1

HCID 574756925-Ethoxypyrazine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 5-ethoxypyrazine-2-carboxylate (0.65 g, approx. purity 85%) was dissolved in dioxan (3 mL) and water (3 mL) was added, followed by lithium hydroxide monohydrate (255 mg, portionwise over 10 mins). After stirring at RT for 24 h, Et2O (25 mL) and NaHCO3 (sat., aq., 25 mL) were added. The layers were separated and the organic layer was extracted with NaOH (1 N, aq., 25 mL). The combined aqueous portions were acidified with 6N HCl to pH 2, and the mixture extracted with EtOAc (3×40 mL). The combined EtOAc extracts were dried over MgSO4 and evaporated to afford the title compound as an off-white powder. 1H NMR (400 MHz, CDCl3) δ ppm 1.47 (t, J=7.1 Hz, 3H), 4.53 (q, J=7.1 Hz, 2H), 8.16 (d, J=1.2 Hz, 1H), 8.98 (d, J=1.2 Hz, 1H)

Workup

  1. customThe layers were separated
  2. extractionthe organic layer was extracted with NaOH (1 N, aq., 25 mL)
  3. extractionthe mixture extracted with EtOAc (3×40 mL)
  4. dry with materialThe combined EtOAc extracts were dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-1ac5b9bff96c4ccf9606a8c91e8fba9f
Source dataset
uspto-grants-2013_11
Patent number
US08592408B2

Reaction notes

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