3-Hydroxyanthranilic Acid → 2-Amino-5-bromo-3-hydroxybenzoic Acid

HRID 17512

Reaction equation

HRID 17512 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH2:11].[Br:12]Br.CO.O>C(O)(=O)C>[NH2:11][C:3]1[C:2]([OH:1])=[CH:10][C:9]([Br:12])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 863-Hydroxyanthranilic AcidHCID 887MethanolHCID 962WaterHCID 24408Bromine

Product 1

HCID 217551432-Amino-5-bromo-3-hydroxybenzoic AcidYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

3-Hydroxyanthranilic acid (6.28 g, 41.0 mmol) was dissolved in acetic acid (550 ml), then a solution of bromine (13.1 g, 82.0 mmol) dissolved in acetic acid (50 ml) was gradually and dropwise added at room temperature, taking 20 minutes. After stirring at room temperature for 2.5 hours, methanol (70 ml) and water (300 ml) were added to the solution, followed by stirring at room temperature for 15 hours. The formed solid was collected by nitration, and dried under reduced pressure to obtain the entitled compound (9.129 g, 97%) as a brown powder.

Workup

  1. additiondropwise added at room temperature
  2. stirringby stirring at room temperature for 15 hours
  3. customThe formed solid was collected by nitration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-4ad1f4d15d514ec0aa6dbe5e8378817a
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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