Bromine → 2-Amino-5-bromonicotinic acid

HRID 2201563Notes

Reaction equation

HRID 2201563 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 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

2-Amino-nicotinic acid (2 g, 14.48 mmol) was dispersed in glacial acetic acid. To this suspension was added a solution of bromine (1.2 mL) in glacial acetic acid (5 mL). The mixture was stirred at room temperature for 20 h. The mixture was filtered and washed with glacial acetic acid (10 mL) and water in several portions. The precipitate was collected and dried to give 2-amino-5-bromonicotinic acid (3.0 g, 95% yield) as yellow solid. 1H-NMR (DMSO-d6, 400 MHz) δ 8.31 (d, J=2.4 Hz, 1H), 8.18 (d, J=2.8 Hz, 1H), 5.06˜5.27 (m, 2H). MS (M+H)+: 218/220.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with glacial acetic acid (10 mL) and water in several portions
  3. customThe precipitate was collected
  4. customdried

Sources & evidence

ORD record
ord-e11486f5666b4baaa454c0cb0eaf49f4
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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