Dimethylformamide → 2-Fluoropyridine-3-carbonyl chloride

HRID 2067097Notes

Reaction equation

HRID 2067097 reaction equation
[F:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.S(Cl)([Cl:13])=O.CN(C)C=O>ClCCl>[F:1][C:2]1[C:7]([C:8]([Cl:13])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 960892-Fluoronicotinic acid

Product 1

HCID 219595822-Fluoropyridine-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Fluoropyridine-3-carboxylic acid (5.02 g, 35.6 mmol) was suspended in dichloromethane (100 mL), treated with thionyl chloride (13.0 mL, 178 mmol, 5 equiv) and N,N-dimethylformamide (0.138 mL, 1.78 mmol, 0.05 equiv) and placed into a preheated oil bath at 45° C. for 2 hours. The mixture was cooled to ambient temperature, concentrated in vacuo and the residue was concentrated from toluene (2×50 mL), providing the titled compound.

Workup

  1. concentrationconcentrated in vacuo
  2. concentrationthe residue was concentrated from toluene (2×50 mL)

Sources & evidence

ORD record
ord-0684152281c747bbbb5c43a68e15066d
Source dataset
uspto-grants-2012_10
Patent number
US08293744B2

Reaction notes

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