Hydrochloric Acid → N-(3-Chloro-2-pyrazinyl)glycine

HRID 1749271Notes

Reaction equation

HRID 1749271 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:5]([NH:10][CH2:11][C:12]([O:14]CC)=[O:13])=[N:6][CH:7]=[CH:8][N:9]=1.Cl>C(O)C>[Cl:3][C:4]1[C:5]([NH:10][CH2:11][C:12]([OH:14])=[O:13])=[N:6][CH:7]=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59336155HCID 59336155, compound

Product 1

HCID 25120491N-(3-Chloro-2-pyrazinyl)glycineYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2N aqueous sodium hydroxide solution (0.6 mL) was added to an ethanol solution (0.3 mL) of Compound 22 (194 mg) and the mixture was stirred at room temperature for 1 hour. 2N hydrochloric acid was then added to the reaction mixture while cooled with ice, and the mixture was neutralized. The product was extracted with chloroform (5 times). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to give 38 mg (23% yield) of the desired product.

Workup

  1. temperaturewhile cooled with ice
  2. extractionThe product was extracted with chloroform (5 times)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f0ac62eed8a4413948fdbd9cf3be525
Source dataset
uspto-grants-2015_10
Patent number
US09156817B2

Reaction notes

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