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

HRID 345030

Reaction equation

HRID 345030 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-nitrophenethyl-amine (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-bef763eb70a0459698faf26f3e4eec1a
Source dataset
uspto-grants-1991_10
Patent number
US05055473

Linked notes

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