4-Amino-3-cyanobenzotrifluoride → HCID 19819671, compound

HRID 1031126Notes

Reaction equation

HRID 1031126 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12]#[N:13].[NH2:14][C:15]1C(C#N)=CC(C(F)(F)F)=CC=1Br>C(OCC)(=O)C>[C:15]([C:7]1[CH:6]=[C:5]([C:8]([F:9])([F:10])[F:11])[CH:4]=[C:3]([C:12]#[N:13])[C:2]=1[NH2:1])#[N:14]

Participants

4

Reactant 2

HCID 126273614-Amino-3-cyanobenzotrifluorideHCID 19779376HCID 19779376, compound

Product 1

HCID 19819671HCID 19819671, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
170 °C

Procedure

A stirred suspension of copper (I) cyanide (3g) and 4-amino-3-bromo-5-cyano-trifluoromethylbenzene (from Preparation 4) (6g) in dry, distilled N-methyl pyrollidinone (50ml) was heated to 170° C. for 16 hours. After cooling to ambient temperature, the reaction mixture was poured into water and ammonium hydroxide, filtered, and the filtrate extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulphate and the solvent evaporated under reduced pressure, to give a yellow oil. Chromatography on silica gel using petroleum ether (boiling range 60-80° C.) containing ethyl acetate (16% by volume) gave 2,6-dicyano-4-trifluoromethyl aniline as a pale yellow solid.

Workup

  1. customin dry
  2. distillationdistilled N-methyl pyrollidinone (50ml)
  3. temperatureAfter cooling to ambient temperature
  4. additionthe reaction mixture was poured into water and ammonium hydroxide
  5. filtrationfiltered
  6. extractionthe filtrate extracted with diethyl ether
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulphate
  8. customthe solvent evaporated under reduced pressure
  9. customto give a yellow oil

Sources & evidence

ORD record
ord-566265c2e843440d98425765e6c9a640
Source dataset
uspto-grants-1992_04
Patent number
US05109004

Reaction notes

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