Oxalyl chloride → Methyl 2-Chloro-6-methylisonicotinate

HRID 1384624Notes

Reaction equation

HRID 1384624 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]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 1412092-Chloro-6-methylpyridine-4-carboxylic acid

Product 1

HCID 2759833Methyl 2-Chloro-6-methylisonicotinateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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. 1H NMR Spectrum: (CDCl3)2.55(s, 3H); 3.90(s, 3H); 7.55(s, 1H); 7.60(s, 1H); MS-ESI: 186 [MH]+

Workup

  1. customThe volatiles were removed by evaporation and methanol (20 ml)
  2. additionadded to the residue
  3. stirringThe mixture was stirred for 1 hour
  4. customthe volatiles removed by evaporation

Sources & evidence

ORD record
ord-94f9ac1efd2d48b3ab77b83afcaa3135
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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