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

HRID 990785Notes

Reaction equation

HRID 990785 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 ethyl acetate (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 ethyl acetate (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-b1403be1d38c4f46a289181831162d92
Source dataset
uspto-grants-2002_10
Patent number
US06462053B1

Reaction notes

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