Ammonium Hydroxide → 2-Fluoro-4-nitroaniline

HRID 418710Notes

Reaction equation

HRID 418710 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. The mixture was cooled to room temperature, and the resulting suspension was diluted in water, shaken for 15 min, the solid was isolated by filtration, rinsed with water, air-dried, and dried under high vacuum to afford title compound 337 (1.76 g, 90% yield) as a yellow crystalline solid. MS (m/z): 157.0 (M+H)+ and 179.0 (M+Na)+.

Workup

  1. customthe solid was isolated by filtration
  2. washrinsed with water
  3. customair-dried
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-451bc4be8ac64b61b0b3573660db605c
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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