Benzene → HCID 18371303, compound

HRID 1731798Notes

Reaction equation

HRID 1731798 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1N.N(OCCC(C)C)=O.[CH:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[F:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 8053Isoamyl NitriteHCID 677852-Fluoro-5-nitroaniline

Product 1

HCID 18371303HCID 18371303, compoundYield 49%

Procedure

2-Fluoro-5-nitroaniline (30 g) was added portionwise over 45 minutes to a refluxing solution of 60 ml isoamyl nitrite in 225 ml benzene. After heating for a further 30 minutes at reflux, the mixture was cooled and the solvent removed by evaporation in vacuo. The residue was triturated many times with hot petroleum ether and the combined extracts were evaporated to give the product as a red oil (19.9 g, yield 49%). This material was used without further purification. NMR (CDCl3, 60MHz): 8.0-8.4 (m, 3H), 7.1-7.6 (m, 5H).

Workup

  1. temperatureAfter heating for a further 30 minutes
  2. temperatureat reflux
  3. temperaturethe mixture was cooled
  4. customthe solvent removed by evaporation in vacuo
  5. customThe residue was triturated many times with hot petroleum ether
  6. customthe combined extracts were evaporated

Sources & evidence

ORD record
ord-292aeaf1fd60412c91192b17ff385df8
Source dataset
uspto-grants-1986_11
Patent number
US04623650

Reaction notes

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