4-Nitroaniline → HCID 22569398, compound

HRID 1394182Notes

Reaction equation

HRID 1394182 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Cl.[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17]Cl>CN(C=O)C>[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH:8][C:7]1[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 74754-NitroanilineHCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 22569398HCID 22569398, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution containing 2.76 g of 4-nitroaniline (20 mmol) in 20 mL DMF was added 1.60 g of NaH (60% dispension in oil, 40 mmol). After 2 hours at room temperature, 2-(dimethylamino)ethyl chloride hydrochloride (3.46 g, 24 mmol) was added, and the reaction mixture was heated at 60° C. for 12 hours. The solvent was evaporated in vacuo to yield a residue which was partitioned between ethyl acetate and brine. The organic phase was dried over anhydrous sodium sulphate, filtered, and concentrated in vacuo to yield a residue. Purification of the residue by flash chromatography with 2% MeOH in CH2Cl2 as the eluent yielded N,N-dimethyl-N′-(4-nitro-phenyl)-ethane-1,2-diamine (2.34 g, 56%) and the title compound (1.23 g, 22%). MS (ES+) m/e 281 [M+H]+.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto yield a residue which
  3. customwas partitioned between ethyl acetate and brine
  4. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a residue
  8. customPurification of the residue by flash chromatography with 2% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-974eb68689ea479fb7ffbff125f5aee3
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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