N-Methyl-4-nitroaniline → N,N,N'-trimethyl-N'-(4-nitrophenyl)-1,2-ethanediamine

HRID 1394180Notes

Reaction equation

HRID 1394180 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([NH:8][CH3:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Cl.[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18]Cl>C1COCC1>[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18][N:8]([CH3:9])[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7483N-Methyl-4-nitroanilineHCID 24758Sodium hydride2×HCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 21873305N,N,N'-trimethyl-N'-(4-nitrophenyl)-1,2-ethanediamineYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution containing 1.52 g of 4-nitro-N-methylaniline (10 mmol) in 30 mL THF, was added 0.8 g of sodium hydride (60% dispension in oil, 20 mmol). After 5 minutes at room temperature, 2.59 g of 2-(dimethylamino)ethyl chloride hydrochloride (18 mmol) and 0.4 g of sodium hydride (60% dispension in oil, 10 mmol) were added. The reaction was heated at 60° C. for 5 hours. The solvent was concentrated in vacuo to yield a residue which was partitioned between ethyl acetate and 2 M sodium hydroxide solution. The organic phase was washed with water (3×), dried over anhydrous sodium sulphate, filtered, and concentrated in vacuo to yield the title compound as a brown oil (1.23 g, 55%). MS (ES+) m/e 224 [M+H]+.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customto yield a residue which
  3. customwas partitioned between ethyl acetate and 2 M sodium hydroxide solution
  4. washThe organic phase was washed with water (3×)
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b824d5853984df1a2efee5aebc22edf
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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