Chlorosuccinimide → Ethyl 4,5-dichloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 15910Notes

Reaction equation

HRID 15910 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]([Cl:12])=[CH:10][C:9](=[O:13])[N:8]([CH3:14])[CH:7]=1)=[O:5])[CH3:2].C1C(=O)N([Cl:22])C(=O)C1>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:11]([Cl:12])=[C:10]([Cl:22])[C:9](=[O:13])[N:8]([CH3:14])[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 11615451Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 11687446Ethyl 4,5-dichloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester (1.00 g, 4.64 mmol) and NCS (0.68 g, 5.10 mmol) in DMF (30 mL) was stirred for 1 hour. The reaction mixture was diluted with EtOAc and washed with 0.1 N HCl solution. The organic layer was dried (MgSO4) and concentrated under reduced pressure to give 1.10 g (95%) of 4,5-dichloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester.

Workup

  1. washwashed with 0.1 N HCl solution
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b22fa8f5e6e24492a355700c274d8c47
Source dataset
uspto-grants-2010_06
Patent number
US07732616B2

Reaction notes

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