Dimethyl Sulfide → 2-Formylpyridine-4-carboxylic acid

HRID 1445706Notes

Reaction equation

HRID 1445706 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][N:11]=1)[C:6]([OH:8])=[O:7])=C.[O:12]=[O+][O-].CSC>CO.C(Cl)Cl>[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][N:11]=1)[C:6]([OH:8])=[O:7])=[O:12]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 17920099HCID 17920099, compound

Product 1

HCID 223237272-Formylpyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 2-vinyl-isonicotinic acid in methanol/DCM 1/1 was cooled to −78° C. and ozone bubbled through it until the solution becomes blue. A stream of nitrogen is then passed through to remove the ozone excess and 1.5 equivalent of methyl sulfide added. The solution was allowed to warm up to room temperature and was concentrated. The product (iic) was then purified by silica flash chromatography.

Workup

  1. customozone bubbled through it until the solution
  2. additionadded
  3. concentrationwas concentrated
  4. customThe product (iic) was then purified by silica flash chromatography

Sources & evidence

ORD record
ord-bebb2dc063f0422599bf5ec5b3c64745
Source dataset
uspto-grants-2010_02
Patent number
US07666870B2

Reaction notes

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