Sodium Hydroxide → 2-Amino-5-(3-hydroxyphenyl)pyrazine

HRID 1249829Notes

Reaction equation

HRID 1249829 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14]C)[CH:9]=2)=[CH:4][N:3]=1.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 218973522-Pyrazinamine, 5-(3-methoxyphenyl)-

Product 1

HCID 226607552-Amino-5-(3-hydroxyphenyl)pyrazineYield 17.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-amino-5-(3-methoxyphenyl)pyrazine (566 mg) was dissolved in methylene chloride (10 mL). To this mixture was added under ice-cooling boron tribromide (530 μL) and the whole was stirred at room temperature for 14 hours. To the reaction mixture was added 1N aqueous sodium hydroxide. The whole was extracted with ethylacetate (30 mL×2). The organic layer was washed with saturated saline solution and then dried over anhydrous Na2SO4. The concentration of the solvent provides the subject compound (94 mg) as a yellow solid.

Workup

  1. additionTo this mixture was added under ice-
  2. extractionThe whole was extracted with ethylacetate (30 mL×2)
  3. washThe organic layer was washed with saturated saline solution
  4. dry with materialdried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-0edcf7b8e9d5447083d6d1d335d11661
Source dataset
uspto-grants-2002_01
Patent number
US06335345B1

Reaction notes

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