3-Cyanobenzoic acid → 3-Cyanobenzoyl chloride

HRID 619260Notes

Reaction equation

HRID 619260 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](O)=[O:11])#[N:6]>CN(C)C=O.ClCCl>[C:5]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([Cl:3])=[O:11])#[N:6]

Participants

5

Reactant 2

HCID 158753-Cyanobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 3084833-Cyanobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (10 ml) and dimethylformamide (1 drop) were added to a solution of 3-cyanobenzoic acid (10 g) in dichloromethane (100 ml), and the mixture was refluxed far 3 hours. After the reaction, the solvent was evaporated under reduced pressure to give 3-cyanobenzoyl chloride. Then, the oil was dissolved in dichloromethane (25 ml), and the solution was dropwise added to a solution of 4-aminopyridine (5 g) and diisopropylethylamine (8.9 g) in dichloromethane (50 ml), which was followed by stirring at room temperature for 1 hour. The precipitated crystals were collected by filtration, and recrystallized from chloroform-methanol-ether to give 5.3 g of N-(4-pyridyl)-3-cyanobenzamide.

Workup

  1. temperaturethe mixture was refluxed far 3 hours
  2. customAfter the reaction
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c8ce1dc885ac468dbbcc2a9e71fbee6e
Source dataset
uspto-grants-1999_09
Patent number
US05958944

Reaction notes

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