Oxalyl chloride → 3-Methoxypyridine-2-carbonyl chloride

HRID 341482Notes

Reaction equation

HRID 341482 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:9]([O-:11])=O)=[N:5][CH:6]=[CH:7][CH:8]=1.[Na+].C(Cl)(=O)C([Cl:16])=O>ClCCl.N1C=CC=CC=1.CN(C=O)C>[CH3:1][O:2][C:3]1[C:4]([C:9]([Cl:16])=[O:11])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 65578Oxalyl chlorideHCID 66803094Sodium 3-methoxypyridine-2-carboxylate2×

Product 1

HCID 867105183-Methoxypyridine-2-carbonyl chlorideYield 28.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of sodium 3-methoxypyridine-2-carboxylate (Intermediate 94, ˜3.3 mmol) in dichloromethane (10 ml) and pyridine (5 ml) at 0 C (ice-bath) was added dropwise oxalyl chloride (0.58 ml, 6.6 mmol). The mixture was stirred 10 minutes, then DMF (1 drop) was added. The mixture was warmed to room temperature and stirred 2 h then concentrated under vacuum. The residue was dissolved in dichloromethane (10 ml) and filtered through a plug of cotton wool. The filtrate was concentrated under vacuum to give the title compound as a brown oil (0.16 g) which was used without further purification or characterisation.

Workup

  1. stirringstirred 2 h
  2. concentrationthen concentrated under vacuum
  3. dissolutionThe residue was dissolved in dichloromethane (10 ml)
  4. filtrationfiltered through a plug of cotton wool
  5. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-4bd8fdbc0380497c8c1eb07265a09966
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

Loading…