Phosphorus oxychloride → 6-Acetyl-7-chloro-1H-pyrazolo[4,3-b]pyridine

HRID 1904270Notes

Reaction equation

HRID 1904270 reaction equation
[C:1]([C:4]1[C:5](=O)[C:6]2[NH:12][N:11]=[CH:10][C:7]=2[NH:8][CH:9]=1)(=[O:3])[CH3:2].P(Cl)(Cl)([Cl:16])=O>>[C:1]([C:4]1[C:5]([Cl:16])=[C:6]2[NH:12][N:11]=[CH:10][C:7]2=[N:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 20038764HCID 20038764, compound

Product 1

HCID 200387626-Acetyl-7-chloro-1H-pyrazolo[4,3-b]pyridine

Conditions

Temperature
80 °C

Procedure

A mixture of 6-acetyl-4,7-dihydro-7-oxo-1H-pyrazolo-[4,3-b]pyridine (D14, 1.6 g, 9 mmol) and phosphorus oxychloride (15 ml) was heated at 80° C. for 30 min. Excess reagent was removed in vacuo, water was added and the mixture was adjusted to pH 9 with 10% sodium carbonate solution. The resulting mixture was extracted with ethyl acetate (4×50 ml), and the extracts were washed with brine, dried (MgSO4) and evaporated in vacuo to leave the title compound as a yellow solid, which was used without further purification.

Workup

  1. customExcess reagent was removed in vacuo, water
  2. additionwas added
  3. extractionThe resulting mixture was extracted with ethyl acetate (4×50 ml)
  4. washthe extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-3905027c93fb47988e88f8bf4cc38228
Source dataset
uspto-grants-1989_06
Patent number
US04837238

Reaction notes

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