Acetone → 4-Amino-2-chlorobenzoic acid

HRID 48006

Reaction equation

HRID 48006 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]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 74482-Chloro-4-nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 171544-Amino-2-chlorobenzoic acid

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

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

  1. filtrationfiltered
  2. customto remove the catalyst
  3. 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

Linked notes

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