HCID 23378469, compound → HCID 23378466, compound

HRID 1018296Notes

Reaction equation

HRID 1018296 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:6]([N+:17]([O-])=O)[C:5]=1[CH3:20]>C1COCC1.CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:6]([NH2:17])[C:5]=1[CH3:20]

Participants

4

Reactant 1

HCID 23378469HCID 23378469, compound

Product 1

HCID 23378466HCID 23378466, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

4-Cyclohexylamino-2-methyl-3-nitrobenzoic acid methyl ester (150 mg) was dissolved in THF/MeOH (30 mL, 1:2 ratio) and stirred in the presence of H2 (1 atm) and a catalytic amount of Pd(OH)2 (20 mg) at room temperature for 14 h. The reaction mixture was then filtered, evaporated to dryness and purified by flash column chromatography, using 25% EtOAc in hexane with 0.2% NH4OH as the eluent, to give the pure aniline (106 mg).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customevaporated to dryness
  3. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-d03d4fcc553b4b57a46c93e0d0e2fab3
Source dataset
uspto-grants-2002_11
Patent number
US06479508B1

Reaction notes

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