Hydrogen Bromide → 2-Amino-5-chloro-3-hydroxybenzoic acid

HRID 969879Notes

Reaction equation

HRID 969879 reaction equation
[NH2:1][C:2]1[C:10]([O:11]C)=[CH:9][C:8]([Cl:13])=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].Br.C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([Cl:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 10340Sodium CarbonateHCID 866072392-Amino-5-chloro-3-methoxybenzoate

Product 1

HCID 180011182-Amino-5-chloro-3-hydroxybenzoic acidYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-amino-5-chloro-3-methoxybenzoate (2.76 g, 12.8 mmol), 48% aqueous solution of hydrobromic acid (25 mL) and glacial acetic acid (1 mL) was heated to reflux for 48 h. The reaction mixture was cooled down to room temperature, treated with saturated solution of Na2CO3 to pH˜6, concentrated and purified by column chromatography (silica gel, 90:10 dichloromethane/methanol) to afford 2-amino-5-chloro-3-hydroxybenzoic acid (0.84 g, 35%) as a light brown solid: MS (ESI+) m/z 188 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 h
  3. concentrationconcentrated
  4. custompurified by column chromatography (silica gel, 90:10 dichloromethane/methanol)

Sources & evidence

ORD record
ord-0e5be3ed41ca4c0da3856d870bf48f1c
Source dataset
uspto-grants-2007_12
Patent number
US07307094B2

Reaction notes

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