2-Fluoro-5-nitrobenzonitrile → 5-Amino-2-fluorobenzonitrile

HRID 1063487Notes

Reaction equation

HRID 1063487 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:3]=1[C:4]#[N:5]>C(OC(=O)C)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 1

HCID 5194172-Fluoro-5-nitrobenzonitrile

Product 1

HCID 27376735-Amino-2-fluorobenzonitrileYield 85.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-fluoro-5-nitrobenzonitrile (2.0 g) in ethylacetate (50 mL) was added stannous chloride dihydrate (27.0 g). The mixture was brought to reflux for 1.5 h and allowed to cool. The mixture was partitioned between ethyl acetate and sodium bicarbonate (sat. in water). The aqueous phase was extracted with ethyl acetate four times. The organic phase was washed with 4×H2O, dried over sodium sulfate, filtered and concentrated to leave 4-fluoro-3-cyanoaniline (1.40 g). CI mass spectrum z (rel. intensity) 137 (M+H, 100).

Workup

  1. temperatureto reflux for 1.5 h
  2. temperatureto cool
  3. customThe mixture was partitioned between ethyl acetate and sodium bicarbonate (sat. in water)
  4. extractionThe aqueous phase was extracted with ethyl acetate four times
  5. washThe organic phase was washed with 4×H2O
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-16ba01fed0e54f57806a0d04d8d2cad5
Source dataset
uspto-grants-2005_11
Patent number
US06965036B2

Reaction notes

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