4-nitrophenyl 4-nitrobenzoate → 4-Aminophenyl 4-aminobenzoate

HRID 1158595Notes

Reaction equation

HRID 1158595 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:21]=[CH:20][C:7]([C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 3470614-nitrophenyl 4-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 154917254-Aminophenyl 4-aminobenzoateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

11.0 g of 4-nitrophenyl 4-nitrobenzoate (38.2 mM) were dissolved in 350 ml of ethyl acetate and 1.0 g of palladium on charcoal (10%) was added. The resulting mixture was hydrogenated at atmospheric pressure until the theoretical amount of hydrogen was consumed. The mixture was then filtered, the cake was washed with ethyl acetate and the filtrate was evaporated to dryness to give 8.71 g (38.2 mM, 99%) of 4-aminophenyl 4-aminobenzoate as slightly beige crystals.

Workup

  1. customwas consumed
  2. filtrationThe mixture was then filtered
  3. washthe cake was washed with ethyl acetate
  4. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-0a9e4faf398c484196c9cf45cfefb593
Source dataset
uspto-grants-2010_10
Patent number
US07811642B2

Reaction notes

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