Hydrochloric Acid → 3-Amino-6-bromopyrazine-2-carboxylic acid

HRID 1959334Notes

Reaction equation

HRID 1959334 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11]C)=[O:10])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[OH-].[Li+].Cl>CO.O>[NH2:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylate

Product 1

HCID 185216003-Amino-6-bromopyrazine-2-carboxylic acidYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

A mixture of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (3 g, 12.93 mmol) and lithium hydroxide (1.548 g, 64.65 mmol) in MeOH (11.74 mL) and H2O (11.74 mL) was heated to 90° C. for 2 hours. The reaction mixture was allowed to cool, neutralised with HCl and diluted with water, and the resultant precipitate collected by filtration (2.2 g, 78% Yield). 1H NMR (400.0 MHz, DMSO) 7.57 (br s, 2H) and 8.39 (s, 1H), 13.41 (br s, 1H) ppm.

Workup

  1. temperatureto cool
  2. filtrationthe resultant precipitate collected by filtration (2.2 g, 78% Yield)

Sources & evidence

ORD record
ord-f806386f0d134fbbb04e723523ad6e0c
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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