Thionyl Chloride → 6-Cyanopyridine-3-carbonyl chloride

HRID 340093Notes

Reaction equation

HRID 340093 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][N:4]=1)#[N:2].S(Cl)([Cl:14])=O>C1(C)C=CC=CC=1.CN(C=O)C>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:14])=[O:8])=[CH:5][N:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 27611086-Cyanopyridine-3-carboxylic acid

Product 1

HCID 235126576-Cyanopyridine-3-carbonyl chlorideYield 99.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

6-Cyano-nicotinic acid (120 mg, 810 μmol) was suspended in toluene (1 mL) and thionyl chloride (119 μL, 1.62 mmol) was added dropwise followed by one drop of DMF. The reaction mixture was refluxed for 2.5 hours and then allowed to cool to room temperature for 18 hours. The solvents were removed in vacuo and the residue was azeotroped with toluene to furnish the title compound as a brown oil (134 mg) which was used in further experiments without purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 2.5 hours
  2. customThe solvents were removed in vacuo
  3. customthe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-a0d68bfd70ad47b1bca584708294992a
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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