1-Chloro-2-nitrobenzene → N-(2-Ethoxyethyl)-2-nitroaniline

HRID 746210

Reaction equation

HRID 746210 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1Cl)([O-:3])=[O:2].[CH2:11]([O:13][CH2:14][CH2:15][NH2:16])[CH3:12]>C(OCC)(=O)C>[CH2:11]([O:13][CH2:14][CH2:15][NH:16][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH3:12]

Participants

4

Reactant 2

HCID 69451-Chloro-2-nitrobenzeneHCID 66970Ethoxyethylamine

Product 1

HCID 13623317N-(2-Ethoxyethyl)-2-nitroanilineYield 107.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of o-nitrochlorobenzene (30 g) and 2-ethoxyethylamine (51 g) is stirred at 130° C. for 3 hours. After allowing to cool, ethyl acetate (150 ml) is added to the reaction mixture, and the ethyl acetate layer is separated, washed three times with saturated aqueous saline, dried over anhydrous magnesium sulfate, and then concentrated. The residue is distilled under reduced pressure to give N-(2-ethoxyethyl)-o-nitroaniline (42.9 g) as a reddish brown liquid, b.p. 144°-145.5° C./1.0 mmHg.

Workup

  1. temperatureto cool
  2. customthe ethyl acetate layer is separated
  3. washwashed three times with saturated aqueous saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-48e43cbef703412dbb45dc5e8243e257
Source dataset
uspto-grants-1986_07
Patent number
US04603130

Linked notes

Loading…