Ammonia → 2-(8-Methyl-3,8-diaza-bicyclo[3.2.1]oct-3-yl)-6-nitro-quinoline

HRID 645349Notes

Reaction equation

HRID 645349 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][NH:5][CH2:6]2.Cl[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([N+:21]([O-:23])=[O:22])[CH:17]=2)[N:12]=1.C(N(C(C)C)CC)(C)C.N>O1CCOCC1>[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][N:5]([C:11]1[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:21]([O-:23])=[O:22])[CH:17]=3)[N:12]=1)[CH2:6]2

Participants

6

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 4229248-Methyl-3,8-diazabicyclo[3.2.1]octaneHCID 109217232-Chloro-6-nitroquinoline

Product 1

HCID 119505912-(8-Methyl-3,8-diaza-bicyclo[3.2.1]oct-3-yl)-6-nitro-quinoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8-methyl-3,8-diazabicyclo[3.2.1]octane (3.8 g, 30 mmol), 2-chloro-6-nitroquinoline (6.2 g, 30 mmol), diisopropylethylamine (10.5 ml, 60 mmol) and dioxane (100 ml) was stirred at reflux for 15 h. Aqueous ammonia (50 ml, 1 M) was added followed by extraction with dichloromethane (3×50 ml). Chromatography on silica gel with methanol:dichloromethane:aqueous ammonia (1:9:1%) as solvent gave the title compound as a solid. Yield 3.1 g (35%). Mp 152.1-154.5° C.

Workup

  1. temperatureat reflux for 15 h
  2. extractionfollowed by extraction with dichloromethane (3×50 ml)

Sources & evidence

ORD record
ord-ea93915a7470426e95c4a8921d5f7dde
Source dataset
uspto-grants-2010_04
Patent number
US07704991B2

Reaction notes

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