2-Chloro-5-methoxy-4-nitrobenzoic acid → 4-Amino-2-chloro-5-methoxybenzoic acid

HRID 2234484Notes

Reaction equation

HRID 2234484 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-])=O)[C:8]([O:14][CH3:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]>CCO.[Pt]>[NH2:11][C:9]1[C:8]([O:14][CH3:15])=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([Cl:1])[CH:10]=1

Participants

4

Reactant 1

HCID 580563702-Chloro-5-methoxy-4-nitrobenzoic acid2×

Product 1

HCID 670035054-Amino-2-chloro-5-methoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

2-chloro-5-methoxy-4-nitro-benzoic acid (Intermediate 218; 762 mg, 3.8 mmol) was dissolved in EtOH (20 mL) and a catalytic amount of 5% Pt on carbon added under an inert atmosphere. The solution was de-gassed and stirred under an atmosphere of hydrogen at room temperature overnight. The catalyst was filtered off and washed with EtOH and solvent evaporated and the resultant material dried under vacuum to yield the title compound as an off-white solid. (617 mg, 98%)

Workup

  1. customThe solution was de-gassed
  2. filtrationThe catalyst was filtered off
  3. washwashed with EtOH and solvent
  4. customevaporated
  5. dry with materialthe resultant material dried under vacuum

Sources & evidence

ORD record
ord-bbe11f1fb4624526a73f895cef25d6b9
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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