Morpholine → 5-Morpholin-4-yl-8-nitro-quinoline

HRID 513812Notes

Reaction equation

HRID 513812 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:8]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2>CS(C)=O.O>[N:1]1([C:8]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[N:13]3)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 2427555-Chloro-8-nitroquinoline

Product 1

HCID 31356775-Morpholin-4-yl-8-nitro-quinolineYield 81%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Morpholine (251.6 μl, 2.88 mmol) was added to a solution of 5-chloro-8-nitro-quinoline 27 (200 mg, 0.96 mmol) in DMSO (2 ml) and the mixture was heated at 100° C. in a sealed tube for 18 h. After cooling, the mixture was diluted with water (10 ml) and the resulting precipitate was collected by filtration. The solid was dried in vacuo to give the title compound (200 mg, 81%) which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate was collected by filtration
  3. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-8b21dc6578694e09b9d724d9dd8b2d68
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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