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

HRID 1024197Notes

Reaction equation

HRID 1024197 reaction equation
[Cl:1][C:2]1[C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.C(Cl)(=O)C([Cl:15])=O>ClCCl>[Cl:1][C:2]1[C:7]([C:8]([Cl:15])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 122639842,6-Dichlorpyridine-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2,6-dichloropyridine-3-carboxylic acid (75, 1.00 g, 0.00521 mol) in dichloromethane (75 mL) was added 2M Oxalyl chloride (2.61 mL, 0.727 g, 0.00573 mol). The solution began to show vigorous gas evolution, which slowed but continued for about 2 hours. The reaction was allowed to continue at room temperature for an additional 3 hours. The reaction was concentrated to give the compound as a brown oil that crystallized on standing (76, 1.09 g, 99%).

Workup

  1. waitto continue at room temperature for an additional 3 hours
  2. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-9d6d90084cf84737884752878c5a7ca7
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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