2-Methoxyethylamine → N-(2-Methoxyethyl)-2-nitroaniline

HRID 1460374Notes

Reaction equation

HRID 1460374 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][O:12][CH2:13][CH2:14][NH2:15]>C(O)CCC>[CH3:11][O:12][CH2:13][CH2:14][NH:15][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 10375425N-(2-Methoxyethyl)-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

To 28.2g of 2-fluoronitrobenzene in 70ml of n-butanol 30.0g of 2-methoxyethylamine were added and the mixture refluxed overnight to give a dark red solution. After cooling the n-butanol was evaporated off and the product extracted into diethyl ether. The diethyl ether was then washed twice with dilute (aqueous) hydrochloric acid, once with dilute (aqueous) sodium carbonate and once with brine. The ether was then dried using magnesium sulphate and evaporated off to give 35g of 2-(2-methoxyethylamino)nitrobenzene as a red liquid.

Workup

  1. temperaturethe mixture refluxed overnight
  2. customto give a dark red solution
  3. customwas evaporated off
  4. extractionthe product extracted into diethyl ether
  5. washThe diethyl ether was then washed twice
  6. additionwith dilute (aqueous) hydrochloric acid
  7. additiononce with dilute (aqueous) sodium carbonate
  8. dry with materialThe ether was then dried
  9. customevaporated off

Sources & evidence

ORD record
ord-83356119afc449c09c359af5f5aa06fc
Source dataset
uspto-grants-1991_12
Patent number
US05071468

Reaction notes

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