Hydrochloric Acid → 3-Amino-5,6-bis(trifluoromethyl)pyrazine-2-carboxylic acid

HRID 2202509Notes

Reaction equation

HRID 2202509 reaction equation
[NH2:1][C:2]1[C:3]([C:16]([O:18]CC)=[O:17])=[N:4][C:5]([C:12]([F:15])([F:14])[F:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1.[OH-].[Na+].O.Cl>CCO>[NH2:1][C:2]1[C:3]([C:16]([OH:18])=[O:17])=[N:4][C:5]([C:12]([F:15])([F:14])[F:13])=[C:6]([C:8]([F:9])([F:10])[F:11])[N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86657667Ethyl 3-amino-5,6-bis(trifluoromethyl)pyrazine-2-carboxylate

Product 1

HCID 584423113-Amino-5,6-bis(trifluoromethyl)pyrazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of ethyl 3-amino-5,6-bis(trifluoromethyl)pyrazine-2-carboxylate (300 mg, 0.990 mmol) in EtOH (10 ml), 2M NaOH (0.495 ml, 0.990 mmol) was added dropwise over 1 minute. After stirring at RT for 30 minutes the reaction mixture was poured into water (30 ml) and the pH was adjusted to pH 4 by addition of 1M HCl. The mixture was extracted with EtOAc (2×50 ml) and the combined organic extracts were washed with brine (30 ml), dried over MgSO4 (5 g), filtered and concentrated in vacuo to afford the title compound as an off white crystalline solid;

Workup

  1. extractionThe mixture was extracted with EtOAc (2×50 ml)
  2. washthe combined organic extracts were washed with brine (30 ml)
  3. dry with materialdried over MgSO4 (5 g)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-206fc468bac44e8b940ddd078c33e1ae
Source dataset
uspto-grants-2016_06
Patent number
US09365552B2

Reaction notes

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