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

HRID 2230490

Reaction equation

HRID 2230490 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-2f45f5962851475fb245b68dd965f766
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Linked notes

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