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

HRID 1929816Notes

Reaction equation

HRID 1929816 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-016742c93f86438bb7309750da700c9f
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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