N-tert-butyl-N-ethoxalyl-2-nitroaniline → N-tert-butyl-N-ethoxalyl-o-phenylenediamine

HRID 358953Notes

Reaction equation

HRID 358953 reaction equation
[C:1]([N:5]([C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([N:5]([C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:12])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 20065638N-tert-butyl-N-ethoxalyl-2-nitroaniline

Product 1

HCID 67794531N-tert-butyl-N-ethoxalyl-o-phenylenediamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-tert-butyl-N-ethoxalyl-2-nitroaniline (45 g) in absolute ethanol (500 ml) was hydrogenated at standard conditions (1 atm.) using 5% Pd/C (5 g) as catalyst. The catalyst was filtered off and the solvent was removed in vacuo. This left an oil, which crystallized upon standing, m.p. 64°-65° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed in vacuo
  3. waitThis left an oil, which
  4. customcrystallized

Sources & evidence

ORD record
ord-e2b09a21cfdd4f33aac8dec710b6d8cb
Source dataset
uspto-grants-1991_03
Patent number
US04999353

Reaction notes

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