Hydrochloric Acid → 1-(6-Chloropyridin-3-yl)ethan-1-one

HRID 976269Notes

Reaction equation

HRID 976269 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6]C(C#N)=[CH:4][N:3]=1.[CH3:10][Mg]Cl.Cl.C([O:16][CH2:17][CH3:18])C>>[C:17]([C:18]1[CH:6]=[CH:7][C:2]([Cl:1])=[N:3][CH:4]=1)(=[O:16])[CH3:10]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 178418332HCID 178418332, compound

Product 1

HCID 27796981-(6-Chloropyridin-3-yl)ethan-1-one

Procedure

31.91 g (230.3 mmol) of 2-chloro-5-cyano-pyridine are placed in 1.6 liters of diethyl ether under nitrogen, and 155 ml (22% in tetrahydrofuran, 456 mmol) of methylmagnesium chloride are added. The red suspension is stirred for 14 h at RT, poured onto 1.6 liters of ice/water and 320 ml of concentrated hydrochloric acid and stirred for 14 h at RT. Extraction with diethyl ether and methylene chloride, drying with MgSO4 and concentration give 5-acetyl-2-chloro-pyridine; Rf =0.46 (hexane:ethyl acetate=2:1).

Workup

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

Sources & evidence

ORD record
ord-5013782d267b448d90a94f1092117fc9
Source dataset
uspto-grants-1997_03
Patent number
US05612340

Reaction notes

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