Dichloromethane → 5-Chloro-2-methylnicotinoyl chloride

HRID 1914665Notes

Reaction equation

HRID 1914665 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-7e8e785170644488b3112ca10bb2ebd5
Source dataset
uspto-grants-2013_12
Patent number
US08614213B2

Reaction notes

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