Water → 5-(Fluoromethyl)pyrazine-2-carboxylic acid

HRID 2045858Notes

Reaction equation

HRID 2045858 reaction equation
[F:1][CH2:2][C:3]1[N:4]=[CH:5][C:6]([C:9]([O:11]C)=[O:10])=[N:7][CH:8]=1.O.O.[OH-].[Li+].CCOCC>O1CCOCC1>[F:1][CH2:2][C:3]1[N:4]=[CH:5][C:6]([C:9]([OH:11])=[O:10])=[N:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 168937Lithium hydroxide, monohydrateHCID 699365032-Pyrazinecarboxylic acid, 5-(fluoromethyl)-, methyl ester

Product 1

HCID 668695845-(Fluoromethyl)pyrazine-2-carboxylic acidYield 82.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 5-(fluoromethyl)pyrazine-2-carboxylate (94 mg) was dissolved in dioxan (1 mL) and water (1 mL) was added, followed by lithium hydroxide monohydrate (60 mg). After stirring at RT for 18 h, Et2O (20 mL) was added and the mixture was then extracted with NaOH (1 N, aq., 2×20 mL). The aqueous portions were acidified with 6N HCl to pH 1, extracted with EtOAc (2×40 mL), the combined organic portions dried over MgSO4 and evaporated to afford the title compound as a white solid (71 mg). 1H NMR (400 MHz, CDCl3) δ ppm 5.70 (d, J=46.2 Hz, 2H), 8.85 (s, 1H), 9.40 (s, 1H)

Workup

  1. extractionthe mixture was then extracted with NaOH (1 N, aq., 2×20 mL)
  2. extractionextracted with EtOAc (2×40 mL)
  3. dry with materialthe combined organic portions dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-e0ca45c19ba448509c7e88b96eb66512
Source dataset
uspto-grants-2013_11
Patent number
US08592408B2

Reaction notes

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