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

HRID 1584420

Reaction equation

HRID 1584420 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-67ee7f6039d041cb937549573f2775af
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Linked notes

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