2-Chloro-5-methoxy-4-nitrobenzoic acid → 4-Amino-2-chloro-5-methoxybenzoic acid
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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- customThe solution was de-gassed
- filtrationThe catalyst was filtered off
- washwashed with EtOH and solvent
- customevaporated
- 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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