N-bromobutanimide → 3-Bromo-2-hydroxy-5-methylpyridine

HRID 1766440Notes

Reaction equation

HRID 1766440 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[Br:9]N1C(=O)CCC1=O>ClCCl>[Br:9][C:4]1[C:5](=[O:8])[NH:6][CH:7]=[C:2]([CH3:1])[CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 704822-Hydroxy-5-methylpyridine

Product 1

HCID 37252613-Bromo-2-hydroxy-5-methylpyridineYield 63.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Methyl-2(1H)-pyridinone (50 g, 0.46 mol) was suspended in dichloromethane (500 mL). N-bromosuccinimide (82 g, 0.46 mol) was added in portions with cooling. Addition was finished after 15 min; the mixture was stirred for 1 h at room temperature and afterwards partitioned between dichloromethane and water. Organic phases were pooled, dried with Na2SO4 and the solvent was evaporated. The residue was purified by crystallization from ethyl acetate to yield 55 g of the title compound as a light yellow solid, mp 156–161° C.

Workup

  1. temperaturewith cooling
  2. additionAddition
  3. customafterwards partitioned between dichloromethane and water
  4. dry with materialdried with Na2SO4
  5. customthe solvent was evaporated
  6. customThe residue was purified by crystallization from ethyl acetate

Sources & evidence

ORD record
ord-f2ff6f818bb845fb9c56d81a82bc564b
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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