N-(2-aminoethyl)-N-(4-nitrophenyl)amine → HCID 66850960, compound

HRID 1910764Notes

Reaction equation

HRID 1910764 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:3]=1.[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][CH2:27][CH2:28][NH2:29])=[CH:22][CH:21]=1)([O-:19])=[O:18]>COCCOCCOC>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:29][CH2:28][CH2:27][NH:26][C:23]2[CH:22]=[CH:21][C:20]([N+:17]([O-:19])=[O:18])=[CH:25][CH:24]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 236318N-(2-aminoethyl)-N-(4-nitrophenyl)amineHCID 576687972-Trifluoromethanesulfonyloxy-4,6-dimethylpyridine

Product 1

HCID 66850960HCID 66850960, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
165 °C

Procedure

To a solution of trifluoro-methanesulfonic acid 4,6-dimethyl-pyridin-2-yl ester (0.6 g, 2.35 mmol) in diglyme (2 mL) was added N*1*-(4-nitro-phenyl)-ethane-1,2-diamine (0.51 g, 2.82 mmol). The reaction mixture was heated to 165° C. for 24 h. The resulting reaction mixture was concentrated under reduced pressure and the residue diluted with chloroform. The organic layer was washed with brine and water and dried over sodium sulfate. The solvent was evaporated and the crude residue was purified by column chromatography (60-120 mesh) using 20% ethyl acetate/petroleum ether as eluent to afford N-(4,6-dimethyl-pyridin-2-yl)-N′-(4-nitro-phenyl)-ethane-1,2-diamine (0.38 g, 55%) as a cream solid.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. additionthe residue diluted with chloroform
  4. washThe organic layer was washed with brine and water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated
  7. customthe crude residue was purified by column chromatography (60-120 mesh)

Sources & evidence

ORD record
ord-ab5c2889ae8d49f9836ee31df11b37fc
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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