Thionyl Chloride → 5-Chlorocarbonyl-pyridine-2-carboxylic acid methyl ester

HRID 1263608Notes

Reaction equation

HRID 1263608 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>>[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

3

Reactant 2

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

Product 1

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

Procedure

Starting material (10(c)) was prepared as follows. Pyridine 2,5-dicarboxylic acid 2-methyl ester (10(a)) (9.0 g; 0.05 mole) was added to stirring thionyl chloride (25 mL) and the mixture refluxed gently for 2.5 hours. The excess thionyl chloride was removed in vacuo and the residual solid azeotroped with toluene (2×25 mL) to give 5-chlorocarbonyl-pyridine-2-carboxylic acid methyl ester (10(b)) which was used crude in the next reaction.

Workup

  1. customwas prepared
  2. temperaturethe mixture refluxed gently for 2.5 hours
  3. customThe excess thionyl chloride was removed in vacuo
  4. customthe residual solid azeotroped with toluene (2×25 mL)

Sources & evidence

ORD record
ord-02a18f63725646e58062432f4ef33761
Source dataset
uspto-grants-2003_04
Patent number
US06541491B1

Reaction notes

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