3-Hydroxy-2-nitropyridine → 5-Bromo-2-nitropyridin-3-ol

HRID 1435854Notes

Reaction equation

HRID 1435854 reaction equation
[Br:1]N1C(=O)CCC1=O.[OH:9][C:10]1[C:11]([N+:16]([O-:18])=[O:17])=[N:12][CH:13]=[CH:14][CH:15]=1>CN(C=O)C>[Br:1][C:14]1[CH:15]=[C:10]([OH:9])[C:11]([N+:16]([O-:18])=[O:17])=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 270573-Hydroxy-2-nitropyridineHCID 67184N-bromobutanimide

Product 1

HCID 534184205-Bromo-2-nitropyridin-3-olYield 115.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-bromosuccinimide (165 g, 0.927 mole) was added portionwise over 5 h to a solution of 3-hydroxy-2-nitropyridine (100.0 g, 0.714 mole) in DMF (1 L) at 0° C. The resulting mixture was stirred at room temperature for 15 hr then was concentrated in vacuo. The residue was taken up in Et2O (500 mL) and stirred for 30 min. The precipitate was removed by suction filtration, and the filtrate was concentrated in vacuo to afford the title compound (180 g): MS (ES) m/e 219 (M+H)+. This material was used without further purification.

Workup

  1. concentrationthen was concentrated in vacuo
  2. stirringstirred for 30 min
  3. customThe precipitate was removed by suction filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7aa3d9963d7544c996e7c825a8e2ef44
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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