Oxalyl chloride → Methyl 2-Chloro-6-methylisonicotinate
Reaction equation
[C:1](Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[CH:11]=[C:10]([CH3:17])[N:9]=1>C(Cl)Cl>[Cl:7][C:8]1[CH:13]=[C:12]([C:14]([O:16][CH3:1])=[O:15])[CH:11]=[C:10]([CH3:17])[N:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Oxalyl chloride (1.9 g, 15 mmol) was added to 2-chloro-6-methyl-pyridine-4-carboxylic acid (1.7 g, 10 mmol) in methylene chloride (30 ml) and the mixture stirred for 2 hours. The volatiles were removed by evaporation and methanol (20 ml) added to the residue. The mixture was stirred for 1 hour and the volatiles removed by evaporation to give methyl 2-chloro-6-methyl-pyridine-4-carboxylate (1.85 g, 100%) as an off-white solid.
Workup
- customThe volatiles were removed by evaporation and methanol (20 ml)
- additionadded to the residue
- stirringThe mixture was stirred for 1 hour
- customthe volatiles removed by evaporation
Sources & evidence
- ORD record
- ord-2c26454951b34c56a5e94adc0feca9dc
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06362336B1
Reaction notes
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