Phosphorus oxychloride → 3-Chloro-6-(pyridin-4-yl)pyridazine

HRID 2234059Notes

Reaction equation

HRID 2234059 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[CH:9][C:10](=O)[NH:11][N:12]=2)=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:10]1[N:11]=[N:12][C:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 27276126-(Pyridin-4-yl)pyridazin-3(2H)-one

Product 1

HCID 130594283-Chloro-6-(pyridin-4-yl)pyridazineYield 64.6%

Conditions

Temperature
100 °C

Procedure

75.6 g 6-Pyridin-4-yl-2H-pyridazin-3-one is added in small portions to 234.5 g phosphorus oxychloride and the resulting mixture stirred for 1 h at 100° C. Diluting in to ice cold water, adjusting the pH 7 with aqueous sodium hydroxide and extraction with dichloromethane yielded 54 g 3-chloro-6-pyridin-4-yl-pyridazine which is used without further purification.

Workup

  1. additionDiluting in to ice cold water
  2. extractionwith aqueous sodium hydroxide and extraction with dichloromethane

Sources & evidence

ORD record
ord-54854aedef57479983591f929d610ffc
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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