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

HRID 376429Notes

Reaction equation

HRID 376429 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(OCC)(=O)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 85.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-fluoro-5-nitrobenzonitrile (2.0 g, 12 mmol) in ethyl acetate(50 mL) was added stannous chloride (27.0 g, 120 mmol). The reaction mixture was stirred at reflux 1.5 h, then cooled to room temperature. Partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate(150 mL). Organic phase was separated and washed with water (5×75 mL), brine (75 mL); dried over sodium sulfate (anhy.); filtered and concentrated to give 2-fluoro-5-aminobenzonitrile (1.4 g) as pure compound.

Workup

  1. temperatureat reflux 1.5 h
  2. customPartitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate(150 mL)
  3. customOrganic phase was separated
  4. washwashed with water (5×75 mL), brine (75 mL)
  5. dry with materialdried over sodium sulfate (anhy.)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8478ae9ce00f4aafb8ce937a724cad71
Source dataset
uspto-grants-2000_02
Patent number
US06020357

Reaction notes

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