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

HRID 444924Notes

Reaction equation

HRID 444924 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-c506ef0ca4b64d538f3473a7f2d4882e
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

Loading…