4,6-dichloro-3-hydroxy-2-nitrobenzoic acid → HCID 10656625, compound

HRID 659989Notes

Reaction equation

HRID 659989 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:12]([O-])=O)[C:3]=1[OH:15]>[Fe].C(O)(=O)C>[NH2:12][C:4]1[C:3]([OH:15])=[C:2]([Cl:1])[CH:10]=[C:9]([Cl:11])[C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 106584324,6-dichloro-3-hydroxy-2-nitrobenzoic acid

Product 1

HCID 10656625HCID 10656625, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4,6-dichloro-3-hydroxy-2-nitrobenzoic acid (1-6) (700 mg, 2.78 mmol), iron powder (400 mg, 7.16 mmol) and glacial acetic acid (13 mL) was heated at 80° C. for 50 minutes, cooled, and the solids filtered off. The filtrate was concentrated to a brown solid. Subsequent SiO2-gel column chromatography (ethyl acetate/HOAc, 100:1-100:3) gave 2-amino-4,6-dichloro-3-hydroxybenzoic acid (1-8) as a light brown solid (582 mg, 94%). —1H NMR (DMSO-d6): δ 6.68 (s); this is consistent with the literature.4

Workup

  1. temperaturecooled
  2. filtrationthe solids filtered off
  3. concentrationThe filtrate was concentrated to a brown solid

Sources & evidence

ORD record
ord-3255be87ff0243c6aa05d3d714feb4ef
Source dataset
uspto-grants-2011_12
Patent number
US08084459B2

Reaction notes

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