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

HRID 467096Notes

Reaction equation

HRID 467096 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-d5c6715615114ebc886c63a092bb9d74
Source dataset
uspto-grants-1992_10
Patent number
US05158964

Reaction notes

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