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

HRID 1367310Notes

Reaction equation

HRID 1367310 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 2 M 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-945d6507b81b4531966a5824d637e170
Source dataset
uspto-grants-2011_02
Patent number
US07893075B2

Reaction notes

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