Chloroacetic Acid → 1(2H)-Pyrazineacetic acid, 2-oxo-

HRID 887113

Reaction equation

[NH:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]1=[O:7].[OH-].[Na+].Cl[CH2:11][C:12]([OH:14])=[O:13].Cl>>[O:7]=[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]1[CH2:11][C:12]([OH:14])=[O:13]

Participants

Reactant 4

HCID 300Chloroacetic Acid

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 727581,2-Dihydropyrazin-2-one

Product 1

HCID 217140981(2H)-Pyrazineacetic acid, 2-oxo-

Conditions

Temperature: 100 °C

Procedure

Pyrazin-2(1H)-one (0.333 g, 3.47 mmol) was added 5 N sodium hydroxide solution (2.1 mL) followed by chloroacetic acid (0.524 g, 5.54 mmol). The reaction mixture was heated at 100° C. for 2 h. After cooled down to ambient temperature, 2 N hydrochloric acid (3.5 mL) was added and the reaction mixture was directly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). The pure fractions were lyophilized overnight to yield the title compound as a yellow solid. LC/MS 155.2 (M+1).

Workup

temperatureAfter cooled down to ambient temperature
customthe reaction mixture was directly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient)

Sources & evidence

ORD record: ord-3cd525f9d558450cb86154a3b5790845
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247415B2

Linked notes

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