Hydrochloric Acid → 1-(2-Chloropyridin-4-yl)ethan-1-one

HRID 724815Notes

Reaction equation

HRID 724815 reaction equation
[Cl:1][C:2]1[CH:7]=C(C#N)[CH:5]=[CH:4][N:3]=1.[CH3:10][Mg]Cl.Cl.C([O:16][CH2:17][CH3:18])C>>[C:17]([C:18]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=1)(=[O:16])[CH3:10]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 5686382-Chloro-4-cyanopyridineHCID 178418332HCID 178418332, compound

Product 1

HCID 131452551-(2-Chloropyridin-4-yl)ethan-1-one

Procedure

24.61 g (177.62 mmol) of 2-chloro-4-cyano-pyridine are placed in 1.25 liters of diethyl ether under nitrogen, and 120 ml (22% in tetrahydrofuran, 353 mmol) of methylmagnesium chloride are added. The red suspension is stirred for 40 hours at RT, poured onto 1.25 liters of ice/water and 250 ml of 6N hydrochloric acid and stirred for 14 hours at RT. Extraction with diethyl ether and methylene chloride, drying with MgSO4 and concentration give 4-acetyl-2-chloro-pyridine; Rf =0.5 (methylene chloride:methanol=9:1).

Workup

  1. stirringstirred for 14 hours at RT
  2. extractionExtraction with diethyl ether and methylene chloride
  3. dry with materialdrying with MgSO4 and concentration

Sources & evidence

ORD record
ord-7d8bd7f3cb5a4f0f8f2b6ce790b7216b
Source dataset
uspto-grants-1998_01
Patent number
US05705502

Reaction notes

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