Oxalyl chloride → Methyl 2-Chloro-6-methylisonicotinate

HRID 1737573Notes

Reaction equation

HRID 1737573 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-pyridine4-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

  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-9bb58be78bfb4176957632310b502e85
Source dataset
uspto-grants-1999_10
Patent number
US05962458

Reaction notes

Loading…