Dimethylformamide → 5-Chlorocarbonyl-pyridine-2-carboxylic acid methyl ester

HRID 975320

Reaction equation

HRID 975320 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([OH:13])=O)=[CH:7][N:6]=1)=[O:4].S(Cl)([Cl:16])=O.CN(C)C=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([Cl:16])=[O:13])=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 5796316-(Methoxycarbonyl)pyridine-3-carboxylic acid

Product 1

HCID 151211775-Chlorocarbonyl-pyridine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

14.5 g (80 mmol) of 2-methoxycarbonylpyridine-5-carboxylic acid are treated with 6.48 ml of thionyl chloride and 2 ml of anhydrous N,N-dimethylformamide in 200 ml of anhydrous toluene. The mixture is heated at 70° C. for 3 h with stirring. It is then concentrated in vacuo and the residue is dissolved in 150 ml of tetrahydrofuran.

Workup

  1. concentrationIt is then concentrated in vacuo
  2. dissolutionthe residue is dissolved in 150 ml of tetrahydrofuran

Sources & evidence

ORD record
ord-b7ff8f5cd07e44dab300a97985b59738
Source dataset
uspto-grants-1997_03
Patent number
US05607954

Linked notes

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