N-methyl-N-(5-nitrobenzoxazol-2-ylmethyl)-4-nitrophenethylamine → N-methyl-N-(5-aminobenzoxazol-2-ylmethyl)-4-aminophenethylamine

HRID 467088

Reaction equation

HRID 467088 reaction equation
[CH3:1][N:2]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=1)[CH2:3][C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:7]=2[N:8]=1>C(O)C.[Ni]>[CH3:1][N:2]([CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=1)[CH2:3][C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:7]=2[N:8]=1

Participants

4

Reactant 1

HCID 19813428N-methyl-N-(5-nitrobenzoxazol-2-ylmethyl)-4-nitrophenethylamine

Product 1

HCID 19813431N-methyl-N-(5-aminobenzoxazol-2-ylmethyl)-4-aminophenethylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

N-Methyl-N-(5-nitrobenzoxazol-2-ylmethyl)-4-nitrophenethylamine (0.78 g, 2.2 mmole) in ethanol (50 ml) containing Raney nickel (0.1 g) was stirred under a hydrogen atmosphere (50 psi=344.7 kPa) for 18 hours, by which time thin layer chromatographic analysis showed that all the starting material had been consumed [silica chromatography plates using methylene chloride/methanol (19:1) as the solvent]. The reaction mixture was then filtered and evaporated to give an oil which was azeotroped with toluene and triturated with ether. The decanted ether was evaporated to give the title compound as an oil, which was used directly without further purification, yield 0.45 g.

Workup

  1. customhad been consumed [silica chromatography plates
  2. filtrationThe reaction mixture was then filtered
  3. customevaporated
  4. customto give an oil which
  5. customwas azeotroped with toluene
  6. customtriturated with ether
  7. customThe decanted ether was evaporated

Sources & evidence

ORD record
ord-dace2b9299704801a9c73581699bb0d7
Source dataset
uspto-grants-1992_10
Patent number
US05158964

Linked notes

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