Ammonia → 5-Fluoro-2-nitroaniline

HRID 722156Notes

Reaction equation

HRID 722156 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CC(C)=O.C(=O)=O.[NH3:19]>>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH2:19])[CH:7]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 679672,4-DifluoronitrobenzeneHCID 18522661Acetone cardice

Product 1

HCID 753995-Fluoro-2-nitroaniline

Procedure

2,4-Difluoronitrobenzene (1.0 eq) was placed in a dry round-bottomed flask equipped with a dry ice condenser charged with acetone/dry ice. Ammonia was condensed into the flask and the resulting solution was stirred at reflux for 7 hours. A yellow precipitate was formed within 1 hour. After 7 hours, the condenser was removed and the liquid ammonia was allowed to evaporate over several hours. The crude product was purified by flash chromatography on silica gel (85:15 hexanes:EtOAc, product at Rf=0.32, contaminant at Rf=0.51). GC/MS m/z 156.1 (M+), Rt 11.16 minutes.

Workup

  1. customequipped with a dry ice condenser
  2. customcondensed into the flask
  3. temperatureat reflux for 7 hours
  4. customA yellow precipitate was formed within 1 hour
  5. customthe condenser was removed
  6. customto evaporate over several hours
  7. customThe crude product was purified by flash chromatography on silica gel (85:15 hexanes:EtOAc, product at Rf=0.32, contaminant at Rf=0.51)

Sources & evidence

ORD record
ord-466cc6c03df74f96a4866231af0c8037
Source dataset
uspto-grants-2006_11
Patent number
US07138409B2

Reaction notes

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