Water → 6-Bromonicotinic acid

HRID 1296001Notes

Reaction equation

HRID 1296001 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[Mn]([O-])(=O)(=O)=[O:10].[K+].[OH2:15]>CCCCCCCC(C([NH3+])(C(CCCCCCC)=O)C(CCCCCCC)=O)=O.[Cl-]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:15])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 5642162-Bromo-5-methylpyridine

Product 1

HCID 2389326-Bromonicotinic acidYield 44%

Reagents, catalysts & solvents 1

HCID 77620884Tricaprylylmethyl ammonium chlorideSolvent

Conditions

Temperature
110 °C

Procedure

After dissolving 2-bromo-5-picoline (100 g, 0.291 mol) in 1000 ml of water, Aliquat336 (2 ml) was added, and then potassium permanganate (251 g, 0.797 mol) was gradually added over a period of 1 hour and 30 minutes while stirring at 110° C. This mixture was further stirred for an hour, the reaction mixture was filtered through celite without cooling and washed with water, and the filtrate was concentrated to approximately half volume under reduced pressure. After adding 48% hydrobromic acid (˜300 ml), the precipitated crystals were filtered, washed with water and dried to yield the title compound (white crystals 52 g, 44%).

Workup

  1. additionwas added
  2. stirringThis mixture was further stirred for an hour
  3. filtrationthe reaction mixture was filtered through celite
  4. temperaturewithout cooling
  5. washwashed with water
  6. concentrationthe filtrate was concentrated to approximately half volume under reduced pressure
  7. additionAfter adding 48% hydrobromic acid (˜300 ml)
  8. filtrationthe precipitated crystals were filtered
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-186709aaa0f34113a20a5e101e3f5abf
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

Loading…