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

HRID 480058Notes

Reaction equation

HRID 480058 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-40eb195e84a940b48e133f8fa0abbfcc
Source dataset
uspto-grants-2003_11
Patent number
US06649624B2

Reaction notes

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