Dimethylformamide → HCID 66674071, compound

HRID 1186758Notes

Reaction equation

HRID 1186758 reaction equation
[Cl:1][C:2]1[N:3]([CH3:13])[C:4](=[O:12])[CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9].CN(C=O)C.C1C(=O)N([Br:26])C(=O)C1>CCOC(C)=O>[Br:26][C:5]1[C:4](=[O:12])[N:3]([CH3:13])[C:2]([Cl:1])=[C:7]([C:8]([O:10][CH3:11])=[O:9])[CH:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 57442171Methyl 2-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 66674071HCID 66674071, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 250-mL round-bottom flask was charged with methyl 2-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (10 g, 50 mmol), DMF (100 mL) and NBS (17.8 g, 100 mmol). The resulting mixture was stirred at room temperature for 8 hours and diluted with EtOAc (100 mL). The organic layer was washed with sat aq. NaHSO3 solution, water, dried (Na2SO4) and concentrated under reduced pressure yielding to desired product as a white solid (13.7 g, 97%)

Workup

  1. washThe organic layer was washed with sat aq. NaHSO3 solution, water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-048ebc293ed14d568b196c160cf8a36f
Source dataset
uspto-grants-2014_03
Patent number
US08673919B2

Reaction notes

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