N-bromobutanimide → HCID 178433466, compound

HRID 726622Notes

Reaction equation

HRID 726622 reaction equation
[C:1]([C:3]1[C:4]([OH:11])=[N:5][C:6]([CH3:10])=[CH:7][C:8]=1[CH3:9])#[N:2].[Br:12]N1C(=O)CCC1=O>CN(C)C=O.O>[Br:12][C:7]1[C:8]([CH3:9])=[C:3]([C:1]#[N:2])[C:4]([OH:11])=[N:5][C:6]=1[CH3:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 178425241HCID 178425241, compound

Product 1

HCID 178433466HCID 178433466, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, a stirred solution of 14.9 grams (0.10 mole) of 3-cyano-2-hydroxy-4,6-dimethylpyridine is cooled in an ice bath and a solution of 18.1 grams (0.10 mole) of N-bromosuccinimide in 50 mL of N,N-dimethylformamide is added dropwise during a 15 minute period. Upon completion of addition the reaction mixture is stirred at ambient temperature for about 72 hours. After this time, the reaction mixture is diluted to 1000 mL with water and filtered to collect a solid. The solid is dried under vacuum, at about 60° C., yielding 22.2 grams of 5-bromo-3-cyano-2-hydroxy-4,6-dimethylpyridine, mp 254°-262° C. The NMR spectrum is consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. filtrationfiltered
  3. customto collect a solid
  4. customThe solid is dried under vacuum, at about 60° C.

Sources & evidence

ORD record
ord-de2a9fe17c004314841cb7380645b1fd
Source dataset
uspto-grants-1998_01
Patent number
US05710157

Reaction notes

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