6-Aminonicotinic acid → 6-Amino-5-bromo-nicotinic acid

HRID 1290921Notes

Reaction equation

HRID 1290921 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[Br:11]Br>C(O)(=O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:9][C:10]=1[Br:11]

Participants

4

Reactant 2

HCID 184966-Aminonicotinic acidHCID 24408Bromine

Product 1

HCID 227420286-Amino-5-bromo-nicotinic acidYield 82.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution of 6-aminonicotinic acid 13.8 g, 0.1 mole) in glacial acetic acid (100 ml), bromine (16 g, 5 ml, 0.1 mole) in acetic acid (20 ml) is added slowly. The reaction mixture is stirred for 8 hours at room temperature and the acetic acid is removed under reduced pressure. The yellow solid residue is dissolved in water and carefully neutralized with 30% NH4OH. The separated solid is filtered and washed with water to give 18 g of solid; mass spectrum: 218 (M+).

Workup

  1. customthe acetic acid is removed under reduced pressure
  2. dissolutionThe yellow solid residue is dissolved in water
  3. filtrationThe separated solid is filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-d152efdbaee045838588e4462dc47aa2
Source dataset
uspto-grants-1998_05
Patent number
US05753648

Reaction notes

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