Dimethylformamide → 2,6-Dichloro-5-fluoro-4-methylnicotinoyl chloride

HRID 1081416Notes

Reaction equation

HRID 1081416 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[C:7]([CH3:13])[C:3]=1[C:4](O)=[O:5].CN(C)C=O.C(Cl)(=O)C([Cl:22])=O>ClCCl>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[C:7]([CH3:13])[C:3]=1[C:4]([Cl:22])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 151303792,6-Dichloro-5-fluoro-4-methylpyridine-3-carboxylic acid

Product 1

HCID 544489232,6-Dichloro-5-fluoro-4-methylnicotinoyl chlorideYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A slurry of 30.8 g (0.147 moles) of 2,6-dichloro-4-methyl-5-fluoronicotinic acid in 200 mL of dichloromethane, containing a catalytic amount of dimethyl formamide, was treated dropwise over a 1-hour period with 19.2 mL (0.22 moles) oxalyl chloride. After 1 hour, the homogenous solution was evaporated in vacuo, diluted with an equal volume of dichloromethane, and evaporated in vacuo to yield 31.6 g of the title compound as an oil.

Workup

  1. customthe homogenous solution was evaporated in vacuo
  2. additiondiluted with an equal volume of dichloromethane
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-685072695b8d4fba8681c56ef9f283e4
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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