1,2-Dichloroethane → 4-(Chloromethyl)-2,6-dimethylpyridine hydrochloride

HRID 1021298Notes

Reaction equation

HRID 1021298 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[C:4]([CH3:10])[N:3]=1.[Cl:11]CCCl.S(Cl)([Cl:17])=O>CN(C=O)C>[ClH:11].[Cl:17][CH2:8][C:6]1[CH:7]=[C:2]([CH3:1])[N:3]=[C:4]([CH3:10])[CH:5]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 24386Thionyl ChlorideHCID 38250772,6-Dimethyl-4-(hydroxymethyl)pyridine

Product 1

HCID 230016454-(Chloromethyl)-2,6-dimethylpyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2,6-Dimethylpyridin-4-yl)methanol (457 mg) was mixed with DCE (8 ml), and thionyl chloride (0.6 ml) and DMF (19 mg) were added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure to obtain 4-(chloromethyl)-2,6-dimethylpyridine hydrochloride (567 mg).

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-760a73fd8d2a4afaab14a6cc84fdab05
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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