N,N′-1,2-Ethanediylbis[4-nitrobenzamide] → Benzamide, N,N'-1,2-ethanediylbis[4-amino-

HRID 616005Notes

Reaction equation

HRID 616005 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([C:8]([NH:10][CH2:11][CH2:12][NH:13][C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Ni].CC(N(C)C)=O>[NH2:1][C:4]1[CH:26]=[CH:25][C:7]([C:8]([NH:10][CH2:11][CH2:12][NH:13][C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 2134211N,N′-1,2-Ethanediylbis[4-nitrobenzamide]HCID 178418361HCID 178418361, compound2×

Product 1

HCID 5088756Benzamide, N,N'-1,2-ethanediylbis[4-amino-

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 31374DimethylacetamideSolvent

Conditions

Temperature
85 °C

Procedure

In a 2 litre volume autoclave for high pressure, N,N'-bis(p-nitrobenzoyl)ethylenediamine (140 g; 0.39 mol), Raney nickel (5 g) and dimethylacetamide (700 ml) are charged, and the atmosphere in the reaction vessel is well replaced by hydrogen. Then, the contents are stirred at 70 to 100° C for about 3 hours while introducing hydrogen (90 kg/cm2) to effect hydrogenation of the nitro group. The reaction mixture is heated to dissolve the produced diamine, Raney nickel is removed off by filtration, and the filtrate is poured into water (5 liters). The resultant precipitate of the diamine is separated and dried to obtain crude crystals (108 g; yield, 93%). Recrystallization from dimethylacetamide (1.5 liters) affords white crystals melting at 293.5° to 295° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. customis removed off by filtration
  3. additionthe filtrate is poured into water (5 liters)
  4. customThe resultant precipitate of the diamine is separated
  5. customdried
  6. customto obtain crude
  7. customcrystals (108 g; yield, 93%)
  8. customRecrystallization from dimethylacetamide (1.5 liters)

Sources & evidence

ORD record
ord-73f63094f64a4eb98a1970ac9dff52bc
Source dataset
uspto-grants-1978_02
Patent number
US04072664

Reaction notes

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