Methanol → Methyl 2,6-dichloropyridine-3-carboxylate

HRID 2080271Notes

Reaction equation

HRID 2080271 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16]O>>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 11106516Methyl 2,6-dichloropyridine-3-carboxylate

Procedure

To a solution of 2,6-dichloronicotinic acid (50 g, 0.26 mol) in methanol (250 mL) was added thionyl chloride (22.7 mL, 0.312 mol) slowly. The mixture was refluxed for 4 hours and concentrated to give methyl 2,6-dichloronicotinate as a white solid in quantitative yield.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f0e23be35fc94c6190844126432f4e91
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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