Ethylamine → HCID 14986025, compound

HRID 2051483Notes

Reaction equation

HRID 2051483 reaction equation
Br[C:2]1[CH:3]=[N+:4]([O-:15])[C:5]2[C:10]([C:11]=1[N+:12]([O-:14])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:16]([NH2:18])[CH3:17]>O1CCCC1>[CH2:16]([NH:18][C:2]1[CH:3]=[N+:4]([O-:15])[C:5]2[C:10]([C:11]=1[N+:12]([O-:14])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:17]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 84235Quinoline, 3-bromo-4-nitro-, 1-oxide

Product 1

HCID 14986025HCID 14986025, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Bromo-4-nitroquinoline-N-oxide (10 g, 0.037 mol) was dissolved in tetrahydrofuran (100 ml). To the solution, ethylamine (5.96 g, 70% in H2O) was added and the mixture was stirred at room temperature for 1 hour. Tetrahydrofuran was distilled off under vacuum from the whole reaction mixture and the residue was dissolved in chloroform. The chloroform layer was washed with water and dried with anhydrous sodium sulfate. Upon isolation and purification by chromatography on a silica gel column using chloroform as a developing solvent, 3-ethylamino-4-nitroquinoline-N-oxide was obtained in an amount of 5.4 g (yield, 62%).

Workup

  1. distillationTetrahydrofuran was distilled off under vacuum from the whole reaction mixture
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customUpon isolation and purification by chromatography on a silica gel column

Sources & evidence

ORD record
ord-dcb63b03ecf64d68a475377311e889a9
Source dataset
uspto-grants-1991_05
Patent number
US05019574

Reaction notes

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