Ammonia → 2-Amino-6-fluoro-3-nitrobenzonitrile

HRID 1258714Notes

Reaction equation

HRID 1258714 reaction equation
[NH3:1].CCO.F[C:6]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[C:10]([F:17])[C:7]=1[C:8]#[N:9]>C1COCC1>[NH2:1][C:6]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[C:10]([F:17])[C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 27370302,6-Difluoro-3-nitrobenzonitrile

Product 1

HCID 679578082-Amino-6-fluoro-3-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of NH3 in EtOH (19 mL, 8.6 M, 160 mmol) was added dropwise to a solution of 2,6-difluoro-3-nitrobenzonitrile (10 g, 54 mmol) in THF (50 mL) at 0° C. under Ar and the resulting mixture was stirred at 0° C. for 1 h. The mixture was concentrated and the residue washed with brine and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated.

Workup

  1. concentrationThe mixture was concentrated
  2. washthe residue washed with brine
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1f7484e7ad5f442db873fb14fef8435f
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

Loading…