Ammonium Chloride → 5-Amino-2-fluorobenzonitrile

HRID 1597173Notes

Reaction equation

HRID 1597173 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([F:12])=[C:8]([CH:11]=1)[C:9]#[N:10])([O-])=O.[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([F:12])=[C:8]([CH:11]=1)[C:9]#[N:10]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 5194172-Fluoro-5-nitrobenzonitrile

Product 1

HCID 27376735-Amino-2-fluorobenzonitrileYield 71%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of 5-nitro-2-fluorobenzonitrile (10 g, 60.2 mmol), Fe powder (17 g, 0.3 mol), and NH4Cl (1.7 g, 30 mmol) in EtOH/H2O (100 mL, 9:1) was heated at reflux in 2 h. The mixture was filtered at hot. The filtrate was concentrated, taken up in H2O, stirred, filtered air-dried to obtain the title solid as a tan solid, (5.0 g, 71%). 1H NMR (400 MHz, DMSO-d6): d 5.54 (s, 2H), 6.85 (m, 2H), 7.16 (t, J=8.1 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux in 2 h
  3. filtrationThe mixture was filtered at hot
  4. concentrationThe filtrate was concentrated
  5. filtrationfiltered
  6. customair-dried

Sources & evidence

ORD record
ord-228752adbad2407bb20ef04fe27175f7
Source dataset
uspto-grants-2001_09
Patent number
US06294531B1

Reaction notes

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