Bromine → 2-Amino-5-bromonicotinic acid

HRID 901544Notes

Reaction equation

HRID 901544 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

25.00 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-4e8af7f1fc6f41388ea7268a657bbac7
Source dataset
uspto-grants-2008_04
Patent number
US07361764B2

Reaction notes

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