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

HRID 345030

Reaktionsgleichung

Reaktionsgleichung von HRID 345030
[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

Komponenten

4

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bef763eb70a0459698faf26f3e4eec1a
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05055473

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