Hydrochloric Acid → (3-Chloropyrazin-2-yl)acetic acid
Reaction equation
C([O:3][C:4](=[O:18])[CH:5]([C:11]1[C:16]([Cl:17])=[N:15][CH:14]=[CH:13][N:12]=1)C(OCC)=O)C.[OH-].[Na+].Cl.C(OCC)C>C(O)C>[Cl:17][C:16]1[C:11]([CH2:5][C:4]([OH:18])=[O:3])=[N:12][CH:13]=[CH:14][N:15]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 2-(3-chloro-pyrazin-2-yl)-malonic acid diethyl ester (10.0 g) in ethanol (100 ml) was added 2M sodium hydroxide (100 ml) and the reaction mixture heated to 60° C. for 4 hours. The reaction mixture was cooled to ambient temperature then poured onto water and 1M hydrochloric acid followed by extraction with ethyl acetate (3×). The combined organic layers were dried (magnesium sulfate), filtered and the filtrate concentrated to give the crude title compound as a yellow solid. The solid was slurried with diethylether to give (3-chloro-pyrazin-2-yl)-acetic acid (4.35 g). MH+=173, RT=0.72 min (Method A).
Workup
- temperatureThe reaction mixture was cooled to ambient temperature
- extractionfollowed by extraction with ethyl acetate (3×)
- dry with materialThe combined organic layers were dried (magnesium sulfate)
- filtrationfiltered
- concentrationthe filtrate concentrated
- customto give the crude title compound as a yellow solid
Sources & evidence
- ORD record
- ord-9bd0462877b64b1f866e74d12d4d9e9c
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962628B2
Reaction notes
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