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

HRID 1935702Notes

Reaction equation

HRID 1935702 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-fdd2ccaee8b0493a9f2072f1bdca46a0
Source dataset
uspto-grants-2002_05
Patent number
US06388077B1

Reaction notes

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