Hydrazine → 2-fluoro-4-nitrophenylhydrazine

HRID 257345Notes

Reaction equation

HRID 257345 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[NH2:12][NH2:13]>C(O)(C)C>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[NH:12][NH2:13]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 38091702-fluoro-4-nitrophenylhydrazineYield 100%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To a solution of 20.0 g (0.126 mole) of 3,4-difluoronitrobenzene in 50 mL of isopropyl alcohol was slowly added a solution of 4.04 g (0.126 mole) of hydrazine in 20 mL of isopropyl alcohol, causing the reaction mixture to become orange. Upon completion of addition, the reaction mixture was heated at reflux for 30 minutes. A yellow solid, m.p. 137°-139° C., was filtered from the reaction mixture. The NMR spectrum of this solid was consistent with 2-fluoro-4-nitrophenylhydrazine. This product was used in Step B without being fully dried, assuming a 100% yield.

Workup

  1. additionUpon completion of addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 30 minutes
  4. filtrationA yellow solid, m.p. 137°-139° C., was filtered from the reaction mixture
  5. customwithout being fully dried

Sources & evidence

ORD record
ord-7f192789699940bbbfee21018a1c3168
Source dataset
uspto-grants-1993_11
Patent number
US05262390

Reaction notes

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