2-(Chloromethyl)-6-nitroquinoline → N-Ethyl-N-(6-nitroquinol-2-ylmethyl)-4-methanesulphonamidophenethylamine

HRID 1031979Notes

Reaction equation

HRID 1031979 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][CH:7]=1)[CH3:2].Cl[CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([N+:29]([O-:31])=[O:30])[CH:25]=2)[N:20]=1>C(O)C>[CH2:1]([N:3]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][CH:7]=1)[CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([N+:29]([O-:31])=[O:30])[CH:25]=2)[N:20]=1)[CH3:2]

Participants

4

Reactant 2

HCID 126651392-(Chloromethyl)-6-nitroquinolineHCID 17890649N-Ethyl-4-methanesulphonamidophenethylamine

Product 1

HCID 19813443N-Ethyl-N-(6-nitroquinol-2-ylmethyl)-4-methanesulphonamidophenethylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Ethyl-4-methanesulphonamidophenethylamine (see Preparation 9(C)--1.7 g, 7.0 mmole) and 2-chloromethyl-6-nitroquinoline (0.78 g, 4.1 mmole) were heated at reflux temperature in ethanol (50 ml) for 4 hours. The solvent was then evaporated and the residue was diluted with aqueous sodium bicarbonate and extracted with methylene chloride. The organic layer was dried (MgSO4), evaporated and the residue was purified by column chromatography on silica eluting with methylene chloride. The product-containing fractions were combined and evaporated to give the title compound as an oil, yield 0.56 g.

Workup

  1. customThe solvent was then evaporated
  2. additionthe residue was diluted with aqueous sodium bicarbonate
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. customthe residue was purified by column chromatography on silica eluting with methylene chloride
  7. customevaporated

Sources & evidence

ORD record
ord-8ec13a690cff47d68b3b5b1783658285
Source dataset
uspto-grants-1990_09
Patent number
US04956382

Reaction notes

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