Bromine → 2-Amino-5-bromonicotinic acid

HRID 2184659Notes

Reaction equation

HRID 2184659 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:11]Br>C(O)(=O)C>[NH2:1][C:2]1[C:3]([C:4]([OH:6])=[O:5])=[CH:7][C:8]([Br:11])=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 729302-Aminonicotinic acid

Product 1

HCID 7374452-Amino-5-bromonicotinic acidYield 99.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-amino-nicotinic acid (10 g, 72.5 mmol) in acetic acid (70 mL) was dropwise added bromine (9.8 mL, 79.8 mmol) at room temperature under nitrogen. Upon completion of the reaction, the solvent was removed in vacuo, the residue triturated with ether and collected on a filter to give 2-amino-5-bromo-3-pyridine carboxylic acid as a yellow solid (15.7 g, 99%): mp 272° C., (decomposed); 1H-NMR (DMSO-d6) δ 8.8-7.8 (bs, 2H), 8.44 (d, 1H, J=2.48 Hz), 8.34 (d, 1H, J=2.48 Hz); MS (EI) m/z 216/218 ([M+H]+, 100%).

Workup

  1. customat room temperature
  2. customUpon completion of the reaction
  3. customthe solvent was removed in vacuo
  4. customthe residue triturated with ether
  5. customcollected on
  6. filtrationa filter

Sources & evidence

ORD record
ord-d692676f60c740618b636b251914aeb6
Source dataset
uspto-grants-2002_06
Patent number
US06399593B1

Reaction notes

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