Water → 1-(5,6-Dichloropyridin-3-yl)ethan-1-one

HRID 1886151Notes

Reaction equation

HRID 1886151 reaction equation
[CH3:1][Li].[Cl:3][C:4]1[C:5]([Cl:13])=[N:6][CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=O.O>CCOCC>[Cl:13][C:5]1[C:4]([Cl:3])=[CH:12][C:8]([C:9](=[O:11])[CH3:1])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2479875,6-Dichloronicotinic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 101980061-(5,6-Dichloropyridin-3-yl)ethan-1-oneYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

62 ml of a 1.6 M solution (100 mmol) of methyllithium in ether are added to a solution of 9.6 g (50 mmol) of 5,6-dichloronicotinic acid in 250 ml of absolute ether at 0° C. When the addition has ended, the mixture is subsequently stirred at 0° C. for a further 30 minutes and 200 ml of water are then added, while cooling with ice. The phases are separated and the aqueous phase is extracted once more with 50 ml of ether. The combined organic phases are dried over sodium sulphate and evaporated. 9 g (95% of theory) of 2,3-dichloro-5-acetylpyridine, melting point 80° C., are obtained.

Workup

  1. additionWhen the addition
  2. temperaturewhile cooling with ice
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted once more with 50 ml of ether
  5. dry with materialThe combined organic phases are dried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-0e93064d9afa44d7a21865232c7ff53e
Source dataset
uspto-grants-1992_09
Patent number
US05149822

Reaction notes

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