Acetic Acid → 4-(4-Amino-2-fluorophenyl)butanenitrile

HRID 1192877Notes

Reaction equation

HRID 1192877 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][CH2:13][C:14]#[N:15].C(O)(=O)C>C(OCC)(=O)C.[Fe]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:11][CH2:12][CH2:13][C:14]#[N:15])=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 576726254-(2-Fluoro-4-nitrophenyl)butanenitrile

Product 1

HCID 576726094-(4-Amino-2-fluorophenyl)butanenitrileYield 83%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
21 °C

Procedure

A solution of compound 4-(2-Fluoro-4-nitrophenyl)butanenitrile (72) (47 mg, 0.23 mmol), Fe (78 mg, 1.40 mmol) and acetic acid (1 mL) in ethyl acetate (3 mL) was heated under reflux for 2 h. The reaction mixture was allowed to cool to 21° C. and then filtered. The organic layer was concentrated and the residue was purified with silica gel column chromatography (dichloromethane:acetone, 9:1) to give desired 4-(4-Amino-2-fluorophenyl)butanenitrile (71) (33 mg, 83%): 1H NMR δ 6.98-7.01 (m, 1H), 6.46-6.52 (m, 2H), 2.70 (t, 2H, J=7.6 Hz) 2.32 (t, 2H, J=7.2 Hz) 1.89-1.98 (m, 2H).

Workup

  1. temperatureunder reflux for 2 h
  2. filtrationfiltered
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified with silica gel column chromatography (dichloromethane:acetone, 9:1)

Sources & evidence

ORD record
ord-44ab47fdb82546c4aa5b600c6c72d5f4
Source dataset
uspto-grants-2014_03
Patent number
US08680291B2

Reaction notes

Loading…