Dichloromethane → N-(2-Ethoxyethyl)-2-nitroaniline

HRID 637010

Reaction equation

HRID 637010 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:11]([O:13][CH2:14][CH2:15][NH2:16])[CH3:12].ClCCl>C(OCC)(=O)C>[CH2:11]([O:13][CH2:14][CH2:15][NH:16][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 69451-Chloro-2-nitrobenzeneHCID 66970Ethoxyethylamine

Product 1

HCID 13623317N-(2-Ethoxyethyl)-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

According to the method of R. Iemura et al., J. Med. Chem., 29 1178-1183 (1986), combine 1-chloro-2-nitrobenzene (69.0 g, 440 mmol) and 2-aminoethyl ethyl ether (102.5 g, 1.15 mol) and heat to reflux. After 18 hours, cool and dilute the reaction mixture with ethyl acetate (400 mL). Extract with brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with dichloromethane to give N-(2-ethoxyethyl)-2-nitroaniline.

Workup

  1. temperatureheat to reflux
  2. temperaturecool
  3. extractionExtract with brine
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue

Sources & evidence

ORD record
ord-5a6ed0c5647449fdb89686f090e95aa3
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Linked notes

Loading…