Bromine → 2-Amino-5-bromonicotinic acid

HRID 1820083Notes

Reaction equation

HRID 1820083 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[N:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 729302-Aminonicotinic acid

Product 1

HCID 7374452-Amino-5-bromonicotinic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

5.00 g (0.181 mol) of 2-aminonicotinic acid were dispersed in 100 ml of glacial acetic acid. To this suspension was added a solution of 12.0 ml (0.23 mol) of bromine in 50 ml of glacial acetic acid. The mixture was stirred at room temperature for 20 hours. The precipitate formed was filtered off and washed with 100 ml of glacial acetic acid in several portions until the filtrate remained colorless. The crude was dried by suction and crystallized from boiling methanol to afford 38.63 g (0.178 mol, 98% yield) of 2-amino-5-bromonicotinic acid as slightly greenish to off-white crystalline needles. 1H-NMR (d6-DMSO) δ: 8.45 [1H] d, 8.34 [1H] d; MS: m/z 217 [MH+].

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered off
  3. washwashed with 100 ml of glacial acetic acid in several portions until the filtrate
  4. customThe crude was dried by suction
  5. customcrystallized

Sources & evidence

ORD record
ord-ebef45ec5259498e97f122a0a4c346f5
Source dataset
uspto-grants-2009_10
Patent number
US07601839B2

Reaction notes

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