Thionyl Chloride → 6-Chloronicotinoyl Chloride

HRID 982146Notes

Reaction equation

HRID 982146 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][N:3]=1.S(Cl)([Cl:13])=O>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:13])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 792226-Chloronicotinic acid

Product 1

HCID 27821656-Chloronicotinoyl Chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To 7.88 g of 6-chloronicotinic acid were added 7.3 ml of thionyl chloride and a few drops of DMF. The mixture was heated under reflux for 2 hours, and then the excess of thionyl chloride was distilled off to give crystals of 6-chloronicotinoyl chloride. A solution of the crystals in 60 ml of tetrahydrofuran was added dropwise to a solution of 15.47 g of 5-aminopentanol in 200 ml of tetrahydrofuran at a temperature below 0° C. The mixture was stirred overnight while gradually raising the temperature to room temperature. The solvent was distilled off and to the residue was added water followed by extraction with ethyl acetate. Then, the extract was washed successively with water and a saturated brine solution, dried over magnesium sulfate. The solvent was distilled off and the residue was recrystallized from ethyl acetate to give 11.24 g of N-(5-hydroxypentyl)-6-chloronicotinamide (yield 93%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. distillationthe excess of thionyl chloride was distilled off

Sources & evidence

ORD record
ord-e5c3aba04cbe4a2e9cbbc316b94e1df8
Source dataset
uspto-grants-1991_02
Patent number
US04994456

Reaction notes

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