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

HRID 968343Notes

Reaction equation

HRID 968343 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-c13d3e324b144b598d1eb1fc78614cba
Source dataset
uspto-grants-2005_10
Patent number
US06958356B2

Reaction notes

Loading…