N-bromobutanimide → Ethyl 5-bromo-6-hydroxy-2-(trifluoromethyl)nicotinate

HRID 2421013Notes

Reaction equation

HRID 2421013 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:4]=[CH:3]1.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:17][C:3]1[C:2](=[O:1])[NH:7][C:6]([C:8]([F:9])([F:10])[F:11])=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18374262Ethyl 6-oxo-2-(trifluoromethyl)-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 57900861Ethyl 5-bromo-6-hydroxy-2-(trifluoromethyl)nicotinateYield 74.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 6-oxo-2-(trifluoromethyl)-1,6-dihydropyridine-3-carboxylate (Organic Process Research and Development 1997, 1, 370-378; 0.10 g) in carbon tetrachloride was added N-bromosuccinimide (0.083 g). The mixture was heated at 80° C. for 24 h. Evaporation and the purification by flash column chromatography gave the subtitle compound as a colourless solid (0.10 g).

Workup

  1. customEvaporation
  2. customthe purification by flash column chromatography

Sources & evidence

ORD record
ord-5f8ac24c12964989851de8bdfe2090f9
Source dataset
uspto-grants-2011_06
Patent number
US07956070B2

Reaction notes

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