Dimethylformamide → 2-Chloronicotinoyl chloride

HRID 710600Notes

Reaction equation

HRID 710600 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CN(C=O)C.S(Cl)([Cl:18])=O>>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:18])=[O:5]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 27745412-Chloronicotinoyl chloride

Conditions

Temperature
70 °C

Procedure

To 2-chloronicotinic acid (15.7 g, 100 mmol) in thionyl chloride (50 mL) was added DMF (0.2 mL), heated to 70° C. and reacted for 3 h. After reaction was complete, solvent was removed by distillation to obtain crude product 17.5 g.

Workup

  1. customreacted for 3 h
  2. customAfter reaction
  3. customsolvent was removed by distillation

Sources & evidence

ORD record
ord-f146a3d838e9420a9777e7ffb2120167
Source dataset
uspto-grants-2015_11
Patent number
US09181244B1

Reaction notes

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