Acetic Acid → 4-Amino-5-bromopyridine-3-carboxylic acid

HRID 520469

Reaction equation

HRID 520469 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1.C(O)(=O)C.[Br:15]Br>O>[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[Br:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 3199794-Aminonicotinic acid

Product 1

HCID 215304944-Amino-5-bromopyridine-3-carboxylic acidYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A sealed tube was charged with 4-aminonicotinic acid 45 (8.00 g, 57.9 mmol), acetic acid (75 mL) and water (75 mL). The reaction was heated at 75° C. and stirred vigorously until homogeneous. After cooling to 50° C., bromine (10.0 mL, 195 mmol) was added and stirring continued for 16 h. Upon cooling to 0° C., the resulting orange precipitate was collected by filtration, rinsed with H2O, and dried under vacuum to give 46 (10.5 g, 84% yield).

Workup

  1. temperatureAfter cooling to 50° C.
  2. stirringstirring
  3. temperatureUpon cooling to 0° C.
  4. filtrationthe resulting orange precipitate was collected by filtration
  5. washrinsed with H2O
  6. customdried under vacuum

Sources & evidence

ORD record
ord-e6fe524ad1694ba8934cf5ce81187a03
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Linked notes

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