Thionyl Chloride → Methyl 6-(chlorocarbonyl)nicotinate

HRID 396269Notes

Reaction equation

HRID 396269 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]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([Cl:16])=[O:13])=[N:9][CH:10]=1)=[O:4]

Participants

3

Reactant 2

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

Product 1

HCID 20707173Methyl 6-(chlorocarbonyl)nicotinate

Procedure

To 5-(Methoxycarbonyl)pyridine-2-carboxylic acid (Maybridge, 1.0 g, 5.52 mmol) was added thionyl chloride (Aldrich, 25 mL) and this reaction mixture was heated to reflux for 2 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure to give the intermediate 5-(methoxycarbonyl)pyridine-2-carboxylic acid chloride as a tan solid which was used without further purification.

Workup

  1. temperaturethis reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0edacadbd6d34e25a491d579548911cd
Source dataset
uspto-grants-2003_08
Patent number
US06608069B1

Reaction notes

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