Acetic Acid → 3-Acetamido-2-phenylpyrazolo[1,5-a]pyridine

HRID 487621Notes

Reaction equation

HRID 487621 reaction equation
[N:1]([C:3]1[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:5][N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12)=O.C(=O)(O)[O-].[Na+].[C:23](O)(=[O:25])[CH3:24]>[Zn]>[C:23]([NH:1][C:3]1[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:5][N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 143735903-Nitroso-2-phenylpyrazolo[1,5-a]pyridine

Product 1

HCID 190924173-Acetamido-2-phenylpyrazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

A mixture of 3-nitroso-2-phenylpyrazolo[1,5-a]pyridine (0.81 g) and zinc powder (0.95 g) in acetic acid (10 ml) was heated under reflux for 2.5 hours. The reaction mixture was poured onto ice-water (100 ml) and neutralized with saturated aqueous sodium bicarbonate solution. Resultant precipitates were collected by filtration, washed with water, and recrystallized from ethyl acetate to give crystals of 3-acetamido-2-phenylpyrazolo[1,5-a]pyridine (304 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. additionThe reaction mixture was poured onto ice-water (100 ml)
  4. customResultant precipitates
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-afabc7ac479e44e1b094a026d1cc713b
Source dataset
uspto-grants-1994_03
Patent number
US05296490

Reaction notes

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