Thionyl Chloride → 6-Chloronicotinoyl Chloride

HRID 928773Notes

Reaction equation

HRID 928773 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:13])=O>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([Cl:13])=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 792226-Chloronicotinic acid

Product 1

HCID 27821656-Chloronicotinoyl Chloride

Procedure

Into a 250-mL round-bottom flask was placed a solution of 6-chloropyridine-3-carboxylic acid (15.8 g, 100.28 mmol) in thionyl chloride (100 mL). The resulting solution was heated to reflux for 5 hours. The resulting mixture was concentrated under vacuum to give the title compound as yellow oil.

Workup

  1. customInto a 250-mL round-bottom flask was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 5 hours
  4. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-fb1aa8b8fc134b1286662d94da068683
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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