Dimethylcarbamoyl Chloride → 6-Cyanopyridine-3-carboxylic acid

HRID 1200024Notes

Reaction equation

HRID 1200024 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N+:4]([O-])[CH:3]=1.C[Si]([C:15]#[N:16])(C)C.CN(C)C(Cl)=O>ClCCl>[C:1]([C:2]1[CH:7]=[CH:6][C:5]([C:15]#[N:16])=[N:4][CH:3]=1)([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 16976Oxiniacic AcidHCID 82115Trimethylsilyl cyanide

Product 1

HCID 27611086-Cyanopyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of nicotinic acid N-oxide (0.7 g, 5 mmol) in 10 ml of dichloromethane is added trimethylsilylcyanide (0.55 g, 5,5 mmol), and the solution is stirred for 5 min. Then dimethylcarbamoyl chloride (0.54 g, 5 mmol) is added, and stirring is continued for 5 days under reflux. After cooling, the solution is evaporated to dryness under reduced pressure, and the residue is dissolved in 50 ml of hot water. After standing overnight, the white precipitate is filtered off and is purified by column chromatography (ethyl acetate/ethanol 1:1) to yield 5-carboxy-2-cyano-pyridine, m.p. 194°-195° C., Rf =0.54.

Workup

  1. stirringstirring
  2. waitis continued for 5 days
  3. temperatureunder reflux
  4. temperatureAfter cooling
  5. customthe solution is evaporated to dryness under reduced pressure
  6. dissolutionthe residue is dissolved in 50 ml of hot water
  7. waitAfter standing overnight
  8. filtrationthe white precipitate is filtered off
  9. customis purified by column chromatography (ethyl acetate/ethanol 1:1)

Sources & evidence

ORD record
ord-f5275898e8d4472b98ee86991096cfc0
Source dataset
uspto-grants-1990_02
Patent number
US04904675

Reaction notes

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