Sodium Hydroxide → 5-Phenoxy-1-phenyl-1H-pyrazolo[3,4-b]pyrazine

HRID 1462598Notes

Reaction equation

HRID 1462598 reaction equation
[OH-:1].[Na+].Cl[C:4]1[N:5]=[C:6]2[CH:12]=[N:11][N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7]2=[N:8][CH:9]=1>C1(O)C=CC=CC=1.C(Cl)(Cl)Cl>[O:1]([C:4]1[N:5]=[C:6]2[CH:12]=[N:11][N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7]2=[N:8][CH:9]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 132719365-Chloro-1-phenyl-1H-pyrazolo[3,4-b]pyrazine

Product 1

HCID 132719485-Phenoxy-1-phenyl-1H-pyrazolo[3,4-b]pyrazineYield 92%

Reagents, catalysts & solvents 2

HCID 996PhenolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

In 5.0 (0.053 mole) of phenol was dissolved 0.34 g (0.0085 mole) of sodium hydroxide, and 1.00 g (0.0043 mole) of 5-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyrazine was added to the solution. The mixture was maintained at 150° C. for 2 hours. The reaction mixture was dissolved in chloroform, and the resulting solution was washed with an aqueous 10% solution of sodium hydroxide and then dried. The solvent was removed by distillation, and the residue was recrystallized from a benzene-hexane mixed solvent to obtain 1.20 g (the yield was 92%) of 5-phenoxy-1-phenyl-1H-pyrazolo[3,4-b]pyrazine in the form of a colorless needle crystal.

Workup

  1. additionwas added to the solution
  2. washthe resulting solution was washed with an aqueous 10% solution of sodium hydroxide
  3. customdried
  4. customThe solvent was removed by distillation
  5. customthe residue was recrystallized from a benzene-hexane mixed solvent

Sources & evidence

ORD record
ord-504a491dcdc5474a846959c9eb60f325
Source dataset
uspto-grants-1984_07
Patent number
US04460773

Reaction notes

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