5-Amino-1-phenyl-4-pyrazolecarboxamide → 7-phenyl-3H,4H,7H-pyrazolo[3,4-d][1,2,3]triazin-4-one

HRID 2073771

Reaction equation

HRID 2073771 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([NH2:15])=[O:14].[N:16]([O-])=O.[Na+]>C(O)(=O)C.Cl.O>[C:7]1([N:6]2[C:2]3[N:1]=[N:16][NH:15][C:13](=[O:14])[C:3]=3[CH:4]=[N:5]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 2

HCID 18025-Amino-1-phenyl-4-pyrazolecarboxamideHCID 23668193Sodium Nitrite

Product 1

HCID 1354231607-phenyl-3H,4H,7H-pyrazolo[3,4-d][1,2,3]triazin-4-oneYield 55%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

1 g of 5-amino-1-phenyl-4-pyrazolecarboxamide in 18 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid was stirred at 0° C. during the addition of a solution of 0.4 g of sodium nitrite in 6 ml of water. The mixture was held at 0° C. for 20 minutes, then allowed to warm to room temperature and stirred for a further 2 hours. The precipitated product was filtered off and recrystallized from ethanol to yield 580 mg of 7-phenyl-7H-pyrazolo[3,4-d]-1,2,3-triazin-4(3H)-one of melting point 150°-151° C.

Workup

  1. filtrationThe precipitated product was filtered off
  2. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a9c07a771fe0445aacec0f121165838e
Source dataset
uspto-grants-1990_04
Patent number
US04920119

Linked notes

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