Triethylamine → N-(morpholin-4-yl)(3-nitroquinolin-4-yl)amine

HRID 1373925Notes

Reaction equation

HRID 1373925 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[NH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].C(Cl)(Cl)Cl>[N:23]1([NH:22][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 20315N-AminomorpholineHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 21075813N-(morpholin-4-yl)(3-nitroquinolin-4-yl)amine

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 4-chloro-3-nitroquinoline (5.00 g, 24.0 mmol) in 100 mL of CH2Cl2 was treated with triethylamine (6.37 mL, 48.0 mmol) and 4-aminomorpholine (3.47 mL, 36.0 mL) under an atmosphere of nitrogen. After 15 h, the reaction mixture was diluted with 5% Na2CO3 solution and CHCl3, and the phases were separated. The organic portion was washed with another portion of 5% Na2CO3 solution, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a bright yellow solid. Recrystallization from acetonitrile gave N-(morpholin4-yl)(3-nitroquinolin-4-yl)amine (4.54 g) as bright yellow needle-like crystals.

Workup

  1. customthe phases were separated
  2. washThe organic portion was washed with another portion of 5% Na2CO3 solution, water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto yield a bright yellow solid
  7. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-e6cb5d6dcbd04057b8944f7ff819ffc4
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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