Methylamine → N-Methyl-5-nitro-2-quinolinamine

HRID 2182668Notes

Reaction equation

HRID 2182668 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-:14])=[O:13])[N:3]=1.[CH3:15][NH2:16]>>[CH3:15][NH:16][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-:14])=[O:13])[N:3]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 3192512-Chloro-5-nitroquinoline

Product 1

HCID 21948796N-Methyl-5-nitro-2-quinolinamine

Procedure

1.0 g (4.8 mmol) of 2-chloro-5-nitroquinoline and 20 ml of 2 M methanolic methylamine solution are heated in a pressure vessel for 8 hours to 120° C. The batch is concentrated by evaporation after the addition of toluene. The residue is purified by column chromatography on silica gel with hexane-ethyl acetate: 580 mg of product.

Workup

  1. concentrationThe batch is concentrated by evaporation
  2. additionafter the addition of toluene
  3. customThe residue is purified by column chromatography on silica gel with hexane-ethyl acetate

Sources & evidence

ORD record
ord-c58bddf5b74f4b13843bc1bbe8540252
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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