Ammonium Chloride → 4-(4-Amino-2-fluorophenyl)butanenitrile

HRID 1504960Notes

Reaction equation

HRID 1504960 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].[NH4+].[Cl-]>O.CO.[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

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 576726254-(2-Fluoro-4-nitrophenyl)butanenitrile

Product 1

HCID 576726094-(4-Amino-2-fluorophenyl)butanenitrileYield 96%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of compound 67 (1.32 g, 6.3 mmol), NH4Cl (5.08 g, 95 mmol) and iron powder (3.52 g, 63 mmol) in water (30 mL) and CH3OH (50 mL) was stirred at 90° C. for 1 h. After cooling, the reaction mixture was filtered and the solid was washed by DCM. The filtrates were separated, the organic layer was washed with brine, dried over Na2SO4 and concentrated to dryness to give compound 68 (1.07 g, 96%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ6.88-6.97 (m, 1H), 6.30-6.44 (m, 1H), 3.65 (br s, 2H), 2.67 (t, 2H, J=7.3 Hz), 2.31 (t, 2H, J=7.2 Hz), 1.86-1.96 (m, 2H).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. washthe solid was washed by DCM
  4. customThe filtrates were separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-354603cbd47a4a4aac0fa7d0df015b56
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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