Toluene → Methyl 5-cyano-3-methylpyridine-2-carboxylate

HRID 2196358Notes

Reaction equation

HRID 2196358 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH3:12])[C:6]([C:9]([OH:11])=[O:10])=[N:7][CH:8]=1)#[N:2].S(Cl)(Cl)=O.[C:17]1(C)C=CC=CC=1>CO>[CH3:17][O:10][C:9]([C:6]1[C:5]([CH3:12])=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=1)=[O:11]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 666658465-Cyano-3-methylpyridine-2-carboxylic acid

Product 1

HCID 66665483Methyl 5-cyano-3-methylpyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-cyano-3-methylpyridine-2-carboxylic acid (2 g, 12.4 mmol) in methanol (20 mL) was added thionyl chloride dropwise under reflux. The mixture was then heated at reflux with stirring. After 60 min, HPLC analysis revealed completion of reaction. To the reaction mixture was added toluene and the mixture was concentrated in vacuo to give the title compound as a pale yellow solid: ESIMS: 177; [(M+H)+]; 1H NMR (400 MHz, DMSO-d6): δ 8.92 (s, 1H), 8.39 (s, 1H), 3.90 (s, 3H), 2.46 (s, 3H).

Workup

  1. temperatureunder reflux
  2. temperatureThe mixture was then heated
  3. temperatureat reflux
  4. customcompletion of reaction
  5. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f185df575c894e129bb04c6d23e34272
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

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