1,2-Bis(4-nitrophenyl)ethane-1,2-dione → 1,2-Bis(4-aminophenyl)-1,2-ethanedione

HRID 1796958Notes

Reaction equation

HRID 1796958 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)=[O:13])=[O:11])=[CH:6][CH:5]=1)([O-])=O>CCO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]([C:12]([C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)=[O:13])=[O:11])=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 18120081,2-Bis(4-nitrophenyl)ethane-1,2-dione

Product 1

HCID 2751371,2-Bis(4-aminophenyl)-1,2-ethanedione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

3.8 g of 4,4′-dinitrobenzil was reduced under hydrogen with 3.8 g 10% Ru on C in EtOH. The mixture was filtered through Supracel and the filtrate concentrated under vacuum to dryness. The residue was dissolved in 50% denatured ethanol in water, treated with Darco and filtered. The filtrate was cooled to 0° C. and the resulting crystals were collected and washed with 50% denatured ethanol in water. The crystals were then dried under a heat lamp to give the title compound as a yellow powder.

Workup

  1. filtrationThe mixture was filtered through Supracel
  2. concentrationthe filtrate concentrated under vacuum to dryness
  3. dissolutionThe residue was dissolved in 50%
  4. additiontreated with Darco
  5. filtrationfiltered
  6. customthe resulting crystals were collected
  7. washwashed with 50%
  8. customThe crystals were then dried under a heat lamp

Sources & evidence

ORD record
ord-28765aa2e30b411d9ebac39517292483
Source dataset
uspto-grants-2006_04
Patent number
US07034026B2

Reaction notes

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