Dichloromethane → 5-Chloro-2-methylnicotinoyl chloride

HRID 2391027Notes

Reaction equation

HRID 2391027 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) is placed in a flask with DCM (100 mL) and oxalyl chloride (3.68 g, 29 mmol). DMF (200 μL) is added and the reaction mixture is stirred at r.t. for 1 hour (gas evolution). The mixture is filtered and the solvent is removed in vacuo to afford the title product which is used in the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-87713bdd813f4ad9ae75404301741760
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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