Bromine → 5-Bromo-4-hydroxy-6-methylpyridine-3-carboxylic acid

HRID 524324Notes

Reaction equation

HRID 524324 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>[Br:12][C:3]1[C:2](=[O:1])[C:7]([C:8]([OH:10])=[O:9])=[CH:6][NH:5][C:4]=1[CH3:11]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 178429106HCID 178429106, compound

Product 1

HCID 183299675-Bromo-4-hydroxy-6-methylpyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-hydroxy-6-methyl-nicotinic acid (10.00 g, 65.3 mmol) in glacial acetic acid (35 mL) is added bromine (4.00 mL, 78.1 mmol). After stirring for 18 h at room temperature, additional bromine (0.5 mL) is added and the reaction mixture is stirred for an additional 24 h. The reaction mixture is evaporated under reduced pressure and the remaining residue is co-evaporated with toluene. The remaining residue is treated with a small amount of MeOH and then triturated with water. The precipitate is filtered off and dried. Yield: 13.8 g (92% of theory); ESI mass spectrum: [M+H]+=232 (bromine isotope pattern); Retention time HPLC: 0.61 min (Z002_002).

Workup

  1. stirringthe reaction mixture is stirred for an additional 24 h
  2. customThe reaction mixture is evaporated under reduced pressure
  3. additionThe remaining residue is treated with a small amount of MeOH
  4. customtriturated with water
  5. filtrationThe precipitate is filtered off
  6. customdried
  7. custom0.61 min (Z002_002)

Sources & evidence

ORD record
ord-ea91c856c71f42268363d17607c29c0c
Source dataset
uspto-grants-2016_05
Patent number
US09340507B2

Reaction notes

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