N,N'-didecyl-5-nitro-1,3-benzenedicarboxamide → 5-amino-N,N'-didecyl-1,3-benzenedicarboxamide

HRID 1757780Notes

Reaction equation

HRID 1757780 reaction equation
[CH2:1]([NH:11][C:12]([C:14]1[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[C:16]([C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:24])[CH:15]=1)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>[Pd].O1CCCC1>[NH2:20][C:18]1[CH:19]=[C:14]([C:12]([NH:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[O:13])[CH:15]=[C:16]([C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:24])[CH:17]=1

Participants

4

Reactant 1

HCID 19388993N,N'-didecyl-5-nitro-1,3-benzenedicarboxamide

Product 1

HCID 193889485-amino-N,N'-didecyl-1,3-benzenedicarboxamideYield 77.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 21 g (0.043 mol) of N,N'-didecyl-5-nitro-1,3-benzenedicarboxamide and 7.0 g of 10% palladium on carbon in 250 ml of tetrahydrofuran was shaken under hydrogen pressure (52 psi initially) on a Parr Hydrogenator for 17 hours. The catalyst was removed by filtration and the solvent was removed from the filtrate at reduced pressure to give a solid which was recrystallized from methanol-water to give 15.3 g (77% yield, mp 188°-189°) of 5-amino-N,N'-didecyl-1,3-benzenedicarboxamide.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed from the filtrate at reduced pressure
  3. customto give a solid which
  4. customwas recrystallized from methanol-water

Sources & evidence

ORD record
ord-def1122a9aba4f7f99c6787fc7d47e00
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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