Phosphorus oxychloride → 3-Chloro-6-(pyridin-2-yl)pyridazine

HRID 499151

Reaction equation

HRID 499151 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[CH:9][C:10](=O)[NH:11][N:12]=1.O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:10]1[N:11]=[N:12][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 49800226-(Pyridin-2-yl)pyridazin-3-ol

Product 1

HCID 64179603-Chloro-6-(pyridin-2-yl)pyridazineYield 45%

Procedure

To a solid 6-pyridin-2-yl-2H-pyridazin-3-one (0.500 g, 2.900 mmol) was added 20 mL of POCl3 and the mixture was stirred at reflux for 4 hours. Excess POCl3 was removed in vacuo. The residue was poured on ice and neutralized using NaHCO3. The product was extracted with ether and ethyl acetate. The combined organic extracts were dried over MaSO4 and evaporated. The residue was purified by column chromatography to afford of 3-chloro-6-pyridin-2-ylpyridazine in 45% yield (0.250 g).

Workup

  1. temperatureat reflux for 4 hours
  2. customExcess POCl3 was removed in vacuo
  3. additionThe residue was poured on ice
  4. extractionThe product was extracted with ether and ethyl acetate
  5. customThe combined organic extracts were dried over MaSO4
  6. customevaporated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8927cc31296542548e6cd2f7ab81a476
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Linked notes

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