2-Phenylpyrazolo[1,5-a]pyridine → HCID 14373590, compound

HRID 487619Notes

Reaction equation

HRID 487619 reaction equation
[N:1]([O-:3])=O.[Na+].[C:5]1([C:11]2[CH:19]=[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]3[N:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O.C(O)(=O)C>[N:1]([C:19]1[C:11]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N:12][N:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=12)=[O:3]

Participants

5

Reactant 2

HCID 156203422-Phenylpyrazolo[1,5-a]pyridineHCID 23668193Sodium Nitrite

Product 1

HCID 14373590HCID 14373590, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of sodium nitrite (533 mg) in water (2.5 ml) was added dropwise to a solution of 2-phenyl-pyrazolo[1,5-a]pyridine (1.0 g) in acetic acid (5 ml) at 13° to 15° C. After being stirred at the same temperature for 20 minutes, the reaction mixture was poured onto ice-water. Resultant precipitates were collected by filtration, washed with water and recrystallized from acetone to give crystals of 3-nitroso-2-phenylpyrazolo[1,5-a]pyridine (0.82 g).

Workup

  1. additionthe reaction mixture was poured onto ice-water
  2. customResultant precipitates
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customrecrystallized from acetone

Sources & evidence

ORD record
ord-1b4f2de4894d4553a7b108bc298fd093
Source dataset
uspto-grants-1994_03
Patent number
US05296490

Reaction notes

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