Potassium Carbonate → N-Methyl-6-nitro-N-[(4-nitrophenoxy)propyl]-2-quinoline-methanamine

HRID 1091096Notes

Reaction equation

HRID 1091096 reaction equation
Cl.[N+:2]([C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][CH2:11][CH2:12][NH:13][CH3:14])=[CH:7][CH:6]=1)([O-:4])=[O:3].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)([O-])[O-].[K+].[K+]>C(#N)C.C(O)C>[CH3:14][N:13]([CH2:12][CH2:11][CH2:10][O:9][C:8]1[CH:15]=[CH:16][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][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

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 126651392-(Chloromethyl)-6-nitroquinolineHCID 67917252N-[3-(4-Nitrophenoxy)propyl]methylamine Hydrochloride

Product 1

HCID 15675923N-Methyl-6-nitro-N-[(4-nitrophenoxy)propyl]-2-quinoline-methanamine

Reagents, catalysts & solvents 1

HCID 21984225Acetonitrile ethanolSolvent

Procedure

N-[3-(4-Nitrophenoxy)propyl]methylamine hydrochloride (3.08 g, 12.49 mmol), 2-(chloromethyl)-6-nitroquinoline (2.78 g, 12.49 mmol), and potassium carbonate (3.45 g, 25.0 mmol) were stirred in 2:1 acetonitrile/ethanol (120 mL) at reflux for 18 hours. The mixture was concentrated and the residue was partitioned between 10% aqueous K2CO3 and 4:1 dichloromethane/isopropanol. The organic phase was dried, decolorized and concentrated to afford crude product which was purified by column chromatography (1:2 hexane/ethyl acetate). Yield: 2.63 g (53%) as a yellow oil.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationThe mixture was concentrated
  3. customthe residue was partitioned between 10% aqueous K2CO3 and 4:1 dichloromethane/isopropanol
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customto afford crude product which
  7. customwas purified by column chromatography (1:2 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-030fda6f03b84193ad184f944c9499a1
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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