Ammonium Hydroxide → 2-Fluoro-4-nitroaniline

HRID 1711103Notes

Reaction equation

HRID 1711103 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[OH-].[NH4+:13]>O>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[NH2:13]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 1012542-Fluoro-4-nitroanilineYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 3,4-difluoronitrobenzene (2.00 g, 12.57 mmol) in ammonium hydroxide (20 ml, 28% in water) was heated at 150° C. in a sealed flask for 3.5 hrs. It was then cooled to room temperature, and the resulting suspension was diluted with water, shaken for 15 min. The resultant precipitate was collected by filtration, rinsed with water, air-dried, and dried under high vacuum to afford title compound 416 (1.76 g, 90% yield) as a yellow crystalline solid. LCMS: 157.0 (M+H)+ and 179.0 (M+Na)+.

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. washrinsed with water
  3. customair-dried
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-bdd4cf240e63496fbb4ea192168bf15b
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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