N-methyl-4-nitrophenethylamine → N-Methyl-N-(6-nitroquinol-2-ylmethyl)-4-nitrophenethylamine

HRID 345037

Reaktionsgleichung

Reaktionsgleichung von HRID 345037
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.Cl[CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=2)[N:17]=1>C(O)C>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)[CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=2)[N:17]=1

Komponenten

4

Edukt 2

HCID 2794239N-methyl-4-nitrophenethylamineHCID 126651392-(Chloromethyl)-6-nitroquinoline

Produkt 1

HCID 19813438N-Methyl-N-(6-nitroquinol-2-ylmethyl)-4-nitrophenethylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

N-Methyl-4-nitrophenethylamine (0.39 g, 2.15 mmole) and 2-chloromethyl-6-nitroquinoline (0.40 g, 2.1 mmole) were heated at reflux temperature in ethanol (30 ml) for 6 hours. The solvent was then evaporated and the residue diluted with 2M hydrochloric acid and extracted with methylene chloride. The aqueous layer was basified with aqueous sodium carbonate (to pH ~12) and extracted three times with methylene chloride. These latter organic extracts were combined, dried (MgSO4) and evaporated giving an oil which was purified by column chromatography on silica eluting with methylene chloride containing methanol (0% up to 1%). The product-containing fractions were combined and evaporated to give a solid which was recrystallised from ethanol to give the title compound, yield 0.21 g, m.p. 104°-105°.

Aufarbeitung

  1. customThe solvent was then evaporated
  2. additionthe residue diluted with 2M hydrochloric acid
  3. extractionextracted with methylene chloride
  4. extractionextracted three times with methylene chloride
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customgiving an oil which
  8. customwas purified by column chromatography on silica eluting with methylene chloride
  9. additioncontaining methanol (0% up to 1%)
  10. customevaporated
  11. customto give a solid which
  12. customwas recrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-f7d9d487619f446dbc231e356ccf31a5
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05055473

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