Acetone → 4-Amino-2-chlorobenzoic acid
Reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[H][H].CC(C)=O>C(O)C.[C].[Pd]>[NH2:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([Cl:1])[CH:10]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
In ethanol (250 mL) was dissolved 100 g (F.W. 201.57, 496 mmol) of 2-chloro-4-nitrobenzoic acid (1) and after replacing with argon, a 10% palladium carbon catalyst (4.0+1.5 g) was added thereto. After replacing with hydrogen, the mixture was stirred at room temperature for 72 hours. The formed crystal was dissolved with acetone and filtered to remove the catalyst. The solvent was distilled under reduced pressure to quantitatively obtain 88 g of the target 4-amino-2-chlorobenzoic acid (2).
Workup
- filtrationfiltered
- customto remove the catalyst
- distillationThe solvent was distilled under reduced pressure to quantitatively obtain 88 g of the target 4-amino-2-chlorobenzoic acid (2)
Sources & evidence
- ORD record
- ord-1a0fb14af5eb4c08bc790f0d9076e4d8
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06700013B2
Reaction notes
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