Thionyl Chloride → 4-Pyridinecarboxylic acid, 3-(chlorocarbonyl)-, methyl ester

HRID 1162561Notes

Reaction equation

HRID 1162561 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]([OH:13])=O)=[O:4].S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]([Cl:16])=[O:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 3275254-(Methoxycarbonyl)pyridine-3-carboxylic acid

Product 1

HCID 140051554-Pyridinecarboxylic acid, 3-(chlorocarbonyl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Chlorocarbonyl-isonicotinic acid methyl ester was prepared by refluxing a mixture of pyridine-3,4-dicarboxylic acid 4-methyl ester (100 mg) and thionyl chloride (75 μl) in chloroform (5 ml) for 3 h. After cooling to room temperature, volatiles were evaporated, and the residue was dried under high vacuum to give the product (100 mg).

Workup

  1. temperatureby refluxing
  2. customvolatiles were evaporated
  3. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-09d26c715f4b4a9eaf26d95e423992c4
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

Loading…