Dichloromethane → 5-Chloro-2-methylnicotinoyl chloride

HRID 75512Notes

Reaction equation

HRID 75512 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(Cl)[Cl:13].C(Cl)(=O)C(Cl)=O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([Cl:13])=[O:8]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 337783875-Chloro-2-methylpyridine-3-carboxylic acid

Product 1

HCID 532566655-Chloro-2-methylnicotinoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloro-2-methyl-nicotinic acid (4.15 g, 24.2 mmol) was placed in a flask with DCM (100 ml) and oxalyl chloride (3.68 g, 29 mmol). DMF (200 μl) was added and the reaction mixture was stirred at RT for 1 hour (gas evolution). The mixture was filtered and the solvent was removed in vacuo to afford the title product which was used without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-39429a4fcf5d4b13a930c6c1311dc9b2
Source dataset
uspto-grants-2014_09
Patent number
US08835444B2

Reaction notes

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