p-Fluoronitrobenzene → N,N,N'-trimethyl-N'-(4-nitrophenyl)-1,2-ethanediamine

HRID 2236692Notes

Reaction equation

HRID 2236692 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][N:12]([CH3:17])[CH2:13][CH2:14][NH:15][CH3:16]>CN1CCCC1=O>[CH3:11][N:12]([CH3:17])[CH2:13][CH2:14][N:15]([CH3:16])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-

Product 1

HCID 21873305N,N,N'-trimethyl-N'-(4-nitrophenyl)-1,2-ethanediamine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluoronitrobenzene (0.35 g, 2.5 mmol) and N,N,N′-trimethylethylenediamine (1.5 g, 1.9 mmol) in N-methylpyrrolidinone (10 mL) is heated for 19 hours in a 100° C. shaking block. After cooling to room temperature, the reaction mixture is partitioned between ethyl acetate and water. The organic phase is washed four times with water and with saturated aqueous sodium chloride solution and then concentrated under reduced pressure to give N,N,N′-trimethyl-N′-(4-nitrophenyl)ethane-1,2-diamine as a brown semisolid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture is partitioned between ethyl acetate and water
  3. washThe organic phase is washed four times with water
  4. concentrationwith saturated aqueous sodium chloride solution and then concentrated under reduced pressure

Sources & evidence

ORD record
ord-175137564f594c7bb0d9b88687c09634
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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