Acetyl chloride → 3-Acetyl-2-methoxypyrazolo[1,5-a]pyridine

HRID 839796Notes

Reaction equation

HRID 839796 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1.[C:12](Cl)(=[O:14])[CH3:13]>>[C:12]([C:11]1[C:3]([O:2][CH3:1])=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 122844272-Methoxypyrazolo[1,5-a]pyridine

Product 1

HCID 122096913-Acetyl-2-methoxypyrazolo[1,5-a]pyridine

Procedure

A mixture of 2-methoxypyrazolo[1,5-a]pyridine (280 mg) acetic anhydride (3 ml) and acetyl chloride (1 ml) was refluxed for 1 hr and the reaction mixture was concentrated under reduced pressure. Water was added to the residue and the solution was made basic with potassium carbonate. The precipitated crystals were collected and washed with water. Recrystallization from n-hexane-ethyl acetate gave colorless needles, mp 158.0°-158.5°. Yield 160 mg.

Workup

  1. temperaturewas refluxed for 1 hr
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. customThe precipitated crystals were collected
  5. washwashed with water
  6. customRecrystallization from n-hexane-ethyl acetate
  7. customgave colorless needles, mp 158.0°-158.5°

Sources & evidence

ORD record
ord-480066229494424ead9b9c019dd0c0dd
Source dataset
uspto-grants-1978_06
Patent number
US04097483

Reaction notes

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