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

HRID 2201574Notes

Reaction equation

HRID 2201574 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-].[Na+].Cl>CO>[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylate

Product 1

HCID 185216003-Amino-6-bromopyrazine-2-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (100 mg, 0.43 mmol) in MeOH (5 mL) was added 2 mL of NaOH aqueous solution (5 N). After being stirred at 50° C. for 4 h, the mixture was cooled and acidified with 1 M HCl to a pH of 2. The precipitate was collected by filtration and washed with water to afford the product of 3-amino-6-bromopyrazine-2-carboxylic acid (90 mg, yield: 96%). 1H-NMR (DMSO-d6, 400 MHz) δ 8.38 (s, 1H), 7.51˜7.56 (m, 2H). MS (M+H)+: 218/220.

Workup

  1. temperaturethe mixture was cooled
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-1d337ffe3d9d4a6c8ece3df6679a0e2c
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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