Bromine → 3-Amino-7-bromo-4-chloro-2-naphthoic acid

HRID 2427096Notes

Reaction equation

HRID 2427096 reaction equation
[NH2:1][C:2]1[C:3]([C:13]([OH:15])=[O:14])=[CH:4][C:5]2[C:10]([C:11]=1[Cl:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.[Br:16]Br>C(O)(=O)C>[NH2:1][C:2]1[C:3]([C:13]([OH:15])=[O:14])=[CH:4][C:5]2[C:10]([C:11]=1[Cl:12])=[CH:9][CH:8]=[C:7]([Br:16])[CH:6]=2

Participants

4

Reactant 2

HCID 24408BromineHCID 122088683-Amino-4-chloro-2-naphthoic acid

Product 1

HCID 668542703-Amino-7-bromo-4-chloro-2-naphthoic acidYield 47.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 0.56 g of 3-amino-4-chloro-2-naphthoic acid and 20 ml of acetic acid was added dropwise 0.4 g of bromine at room temperature. The resulting mixture was stirred at room temperature for 1 hour. A deposited precipitate was collected by filtration, and the resulting solid was washed successively with acetic acid and ethyl acetate to obtain 0.36 g of 3-amino-7-bromo-4-chloro-2-naphthoic acid of the formula:

Workup

  1. filtrationA deposited precipitate was collected by filtration
  2. washthe resulting solid was washed successively with acetic acid and ethyl acetate

Sources & evidence

ORD record
ord-d50bb266cd874cd4bdfc0ab03a3c758a
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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