1-Fluoro-2-nitrobenzene → N-(4-methoxybenzyl)-2-nitroaniline

HRID 861910Notes

Reaction equation

HRID 861910 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][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1>O1CCCC1>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH:18][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 738951-Fluoro-2-nitrobenzeneHCID 754524-Methoxybenzylamine

Product 1

HCID 2920606N-(4-methoxybenzyl)-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-fluoro-2-nitrobenzene (20 g) and 4-methoxybenzylamine (18.52 ml) in dry tetrahydrofuran (100 ml) was stirred at 23° for 18 h under a nitrogen atmosphere. The mixture was filtered, then the organic layer was concentrated in vacuo to an oil. Ethanol (50 ml) was added and a solid separated. After filtration, the title compound was obtained as an orange solid (16.35 g). The filtrate was concentrated in vacuo and the residue was treated with further ethanol (10 ml) to give a further amount of title compound (7.9 g). M.p. 81°-2° T.l.c. CH-EA (8:2), Rf 0.55.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe organic layer was concentrated in vacuo to an oil
  3. additionEthanol (50 ml) was added
  4. customa solid separated
  5. filtrationAfter filtration

Sources & evidence

ORD record
ord-337dcbbc724b49b79329b42700467fb7
Source dataset
uspto-grants-1998_02
Patent number
US05716953

Reaction notes

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