Ammonia → 4-Amino-2,5-difluorobenzonitrile

HRID 1421398Notes

Reaction equation

HRID 1421398 reaction equation
[F:1][C:2]1[CH:9]=[C:8](F)[C:7]([F:11])=[CH:6][C:3]=1[C:4]#[N:5].[NH3:12]>O1CCCC1>[C:4]([C:3]1[C:2]([F:1])=[CH:9][C:8]([NH2:12])=[C:7]([F:11])[CH:6]=1)#[N:5]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 5938132,4,5-Trifluorobenzonitrile

Product 1

HCID 27359004-Amino-2,5-difluorobenzonitrileYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

515 g of 2,4,5-trifluorobenzonitrile in 2000 ml of tetrahydrofuran are introduced into an autoclave and heated to 100° C. 250 ml of liquid ammonia are then pumped in at such a rate that the temperature remains in the range from 100 to 105° C. The mixture is then stirred at this temperature for 8 h and then cooled. The pressure reaches a maximum of 22 bar gauge. After the ammonia has been blown off, the solvent is removed using a rotary evaporator. The residue is stirred into 500 ml of water and placed on a suction filter. After filtering with suction, the residue is again slurried with 200 ml of water and filtered with suction. Drying in a vacuum at 40° C. gives 482 g (95.4% of theory) of 4-cyano-2,5-difluoroaniline having a melting point of from 99 to 100° C.

Workup

  1. customremains in the range from 100 to 105° C
  2. temperaturecooled
  3. customthe solvent is removed
  4. customa rotary evaporator
  5. stirringThe residue is stirred into 500 ml of water
  6. filtrationfilter
  7. filtrationAfter filtering with suction
  8. filtrationfiltered with suction
  9. customDrying in a vacuum at 40° C.

Sources & evidence

ORD record
ord-5a5951dd23b54051b15c6c51b1eac411
Source dataset
uspto-grants-2000_06
Patent number
US06075160

Reaction notes

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