N-bromobutanimide → Ethyl 2-bromo-6-(1,1-dimethylethyl)-3-hydroxy-4-pyridinecarboxylate

HRID 735802Notes

Reaction equation

HRID 735802 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[C:10]([OH:11])=[CH:9][N:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=1)[CH3:2].[Br:17]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:6]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:9]([Br:17])[C:10]=1[OH:11])[CH3:2]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 58980622HCID 58980622, compound

Product 1

HCID 58980648Ethyl 2-bromo-6-(1,1-dimethylethyl)-3-hydroxy-4-pyridinecarboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the above isonicotinic acid ethyl ester (2.0 g, 9.47 mmol) in DMF (20 mL) was added N-bromosuccinimide (1.85 g, 10.4 mmol). The solution was stirred at room temperature for 0.5 h then poured into saturated aqueous NaHCO3. The aqueous layer was extracted with diethyl ether and the combined organic layers were washed with saturated aqueous NaHCO3, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 2-bromo-6-tert-butyl-3-hydroxy-isonicotinic acid ethyl ester (2.74 g, 96%) as a pale yellow oil which was utilized without further purification.

Workup

  1. extractionThe aqueous layer was extracted with diethyl ether
  2. washthe combined organic layers were washed with saturated aqueous NaHCO3
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-81c9bb463bae45d7a92fa3b1b3b274e9
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

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