Bromine → HCID 178432818, compound

HRID 1931218Notes

Reaction equation

HRID 1931218 reaction equation
[OH:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[C:4]([CH3:11])[CH:3]=1.[Br:12]Br>C(O)(=O)C.O>[Br:12][C:3]1[C:4]([CH3:11])=[N:5][CH:6]=[C:7]([C:2]=1[OH:1])[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 24408BromineHCID 178429106HCID 178429106, compound

Product 1

HCID 178432818HCID 178432818, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

4-Hydroxy-6-methylnicotinic acid 19 (95.6 g, 0.625 mol) was dissolved in acetic acid (950 ml) and water (190 ml), and bromine (39 ml, 0.750 mol) was added over 15 minutes. After the solution was stirred at 60° C. for 5 hours, the solvent was distilled off under reduced pressure, methanol (200 ml) was added and, crystals were collected by filtration. The solution was distilled off under reduced pressure, methanol was added again to the residue, and crystals were collected by filtration. A total of 142.2 g (98%) of 5-bromo-4-hydroxy-6-methylnicotinic acid 20 was obtained as a colorless crystal.

Workup

  1. distillationthe solvent was distilled off under reduced pressure, methanol (200 ml)
  2. additionwas added
  3. filtrationcrystals were collected by filtration
  4. distillationThe solution was distilled off under reduced pressure, methanol
  5. additionwas added again to the residue, and crystals
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-f43285c516d9484a95a3691547922a55
Source dataset
uspto-grants-2012_05
Patent number
US08188271B2

Reaction notes

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