Thionyl Chloride → Methyl 6-(chlorocarbonyl)nicotinate

HRID 2189975Notes

Reaction equation

HRID 2189975 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)=[O:4].S(Cl)([Cl:16])=O>>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:6]=[CH:7][C:8]([C:11]([Cl:16])=[O:13])=[N:9][CH:10]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acid

Product 1

HCID 20707173Methyl 6-(chlorocarbonyl)nicotinate

Conditions

Temperature
80 °C

Procedure

A mixture of pyridine-2,5-dicarboxylic acid 5-methyl ester (150 mg, 0.828 mmol) and thionyl chloride (1 mL) was heated at 80° C. for 5 h. The thionyl chloride was evaporated under reduced pressure, the residue was dried in high vacuum and used crude for the next reaction.

Workup

  1. customThe thionyl chloride was evaporated under reduced pressure
  2. customthe residue was dried in high vacuum
  3. customfor the next reaction

Sources & evidence

ORD record
ord-8857c10206db4311a11b0e99d107839e
Source dataset
uspto-grants-2012_12
Patent number
US08324250B2

Reaction notes

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