Hydrochloric Acid → 4-Benzyl-3-oxo-3,4-dihydropyrazine-2-carboxylic acid

HRID 2241302Notes

Reaction equation

HRID 2241302 reaction equation
[Li+].[OH-].[CH2:3]([N:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]([O:18]C)=[O:17])[C:11]1=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.O>C1COCC1.CO>[CH2:3]([N:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]([OH:18])=[O:17])[C:11]1=[O:20])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 67348566Methyl 4-benzyl-3-oxo-3,4-dihydropyrazine-2-carboxylate

Product 1

HCID 673467874-Benzyl-3-oxo-3,4-dihydropyrazine-2-carboxylic acidYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (0.82 mL, 0.82 mmol, 1.0 M in H2O) was added to a solution of methyl 4-benzyl-3-oxo-3,4-dihydropyrazine-2-carboxylate (100 mg, 0.41 mmol) in a mixture of THF (4.5 mL) and MeOH (1.5 mL) at ambient temperature for 4 hours. The reaction mixture was acidified to pH 1 with aqueous 1 N HCl solution and treated with water (5 mL), extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated to afford 77 mg (82%) of the desired product.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-352012ced70849c8a6058063c40ef0cb
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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