4-Ethyl-3-nitrobenzoic acid → 3-Amino-4-ethylbenzoic acid

HRID 1072844

Reaction equation

HRID 1072844 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-])=O)[CH3:2]>CO.[Pd]>[NH2:12][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:3]=1[CH2:1][CH3:2])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 81670864-Ethyl-3-nitrobenzoic acid

Product 1

HCID 124650433-Amino-4-ethylbenzoic acidYield 70.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Ethyl-3-nitrobenzoic acid (5.0 g, 27.4 mmol) was dissolved in methanol (50 ml) and a Pd-C catalyst (5%, 250 mg) was added thereto. The mixture was stirred under a hydrogen atmosphere from 0° C. to room temperature for 1 hr. After the completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. The obtained crystals were washed with methyl t-butyl ether/hexane and dried to give the object compound (3.2 g, 70.6%).

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washThe obtained crystals were washed with methyl t-butyl ether/hexane
  5. customdried

Sources & evidence

ORD record
ord-ea3ac270a21f4d0982e6ac4673865ffc
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Linked notes

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