Ammonium Hydroxide → 2-Amino-3,6-difluorobenzonitrile

HRID 2386899Notes

Reaction equation

HRID 2386899 reaction equation
F[C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5].[OH-].[NH4+:13]>C(#N)C>[NH2:13][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 1456222,3,6-Trifluorobenzonitrile

Product 1

HCID 450905912-Amino-3,6-difluorobenzonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,3,6-Trifluorobenzonitrile (15 g) in ammonium hydroxide solution (28% in water; 80 mL) and acetonitrile (40 mL) was stirred at 70° C. in a pressure vessel for 16 h and the reaction was complete based on GC-MS. Acetonitrile was removed under reduced pressure, and water was added. The white solid precipitate was suction filtered, washed with water and dried under house vacuum over a weekend at room temperature to give 13.7 g (93%) of the crude product; M.P. 90-92° C. GC/MS: m/z 154. 1H NMR (CDCl3): δ 7.07-7.16 (m, 1H), 6.36-6.43 (m, 1H), 4.65 (br s, 2H).

Workup

  1. customAcetonitrile was removed under reduced pressure, and water
  2. additionwas added
  3. filtrationfiltered
  4. washwashed with water
  5. customdried under house vacuum over a weekend at room temperature

Sources & evidence

ORD record
ord-02f7ad8131d74654b2ef8df1b585631f
Source dataset
uspto-grants-2012_09
Patent number
US08268843B2

Reaction notes

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