Dimethylformamide → 2,6-Dichlorpyridine-3-carbonyl chloride

HRID 456625Notes

Reaction equation

HRID 456625 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[Cl:7][C:8]1[N:16]=[C:15]([Cl:17])C=C[C:9]=1[C:10](O)=O.CN(C)C=O>C(Cl)Cl>[Cl:17][C:15]1[N:16]=[C:8]([Cl:7])[CH:9]=[CH:10][C:1]=1[C:2]([Cl:4])=[O:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 122639842,6-Dichlorpyridine-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (2M solution, 20 mL) (Aldrich, Milwaukee, Wis.) was added to a mixture of 2,6-dichloronicotinic acid (6.2 g) and N,N-dimethylformamide (DMF) (0.5 mL) in DCM (100 mL) at room temperature. After stirring at room temperature for 2 hours, the reaction was concentrated to give 2,6-dichloro-nicotinoyl chloride (used directly in the next step).

Workup

  1. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-afd9ff76ff0b46ecbb6e80746e2c5fe9
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

Loading…