1-(4-Amino-3-nitrophenyl)propan-1-one → 1-(3,4-Diaminophenyl)propan-1-one

HRID 626235Notes

Reaction equation

HRID 626235 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][C:3]=1[N+:12]([O-])=O>CO.[Pd]>[NH2:12][C:3]1[CH:4]=[C:5]([C:8](=[O:11])[CH2:9][CH3:10])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 896728871-(4-Amino-3-nitrophenyl)propan-1-one

Product 1

HCID 202165581-(3,4-Diaminophenyl)propan-1-oneYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(4-amino-3-nitrophenyl)propan-1-one (1.94 g, 10 mmol) in 50 mL of methanol was added 0.5 g 10% Pd/C and the mixture was hydrogenated under H2 (1 atm) at rt for 1 h. The mixture was filtered and the filtrated was concentrated to give the desired product (1.48 g, 90%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrated was concentrated

Sources & evidence

ORD record
ord-49f40f8b37384c6aacd54554f6d4a0a7
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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