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

HRID 2241245Notes

Reaction equation

HRID 2241245 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>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 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 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

LiOH (0.82 mL, 0.82 mmol, 1.0 M) was added to a solution of methyl 4-benzyl-3-oxo-3,4-dihydropyrazine-2-carboxylate (0.10 g, 0.41 mmol) in a mixture of THF-MeOH (3:1 ratio, 6 mL) at room temperature. After stirring for 4 hours, 1 N HCl (0.9 mL) was added. The reaction mixture was extracted with EtOAc, dried over MgSO4, and concentrated to give the desired product (0.077 g, 82%). 1H NMR (400 MHz, CD3OD) δ 8.0 (d, 1H), 7.68 (d, 1H), 7.36-7.42 (m, 5H), 5.29 (s, 2H).

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b999e89003f14b9caa67b5a69f4f78cb
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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