Water → 2-Amino-6-(trifluoromethyl)benzonitrile

HRID 1283785Notes

Reaction equation

HRID 1283785 reaction equation
[N:1]1C=CC=C[CH:2]=1.[NH2:7][C:8]1[C:9](Br)=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:12][CH:13]=1.[C-]#N.[Na+].O>C1C=CC=CC=1>[C:2]([C:9]1[C:10]([C:14]([F:17])([F:16])[F:15])=[CH:11][CH:12]=[CH:13][C:8]=1[NH2:7])#[N:1]

Participants

6

Reactant 4

HCID 962WaterHCID 1049Pyridine2×HCID 8929Sodium CyanideHCID 940582-Bromo-3-(trifluoromethyl)aniline

Product 1

HCID 226251952-Amino-6-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 21 g. of dry pyridine is added slowly with stirring 23 g. (0.26 mol.) of cuprous cyanide. The mixture rapidly solidifies and is then heated to 125°. Excess pyridine is boiled off and the temperature is decreased to 110°. 3-Amino-2-bromobenzotrifluoride (48 g., 0.20 mol.) is added with stirring and the reaction mixture is heated to 165°-170° for 75 minutes. The mixture is then cooled to 90° and a solution of 75 g. (1.05 mol.) of sodium cyanide in 75 ml. of water is added followed by 250 ml. of benzene. The resulting mixture is stirred for one hour, the layers are separated and the benzene layer is washed with water, dried and evaporated to give 2-cyano-3-trifluoromethylaniline.

Workup

  1. temperatureis then heated to 125°
  2. customis decreased to 110°
  3. stirringwith stirring
  4. temperaturethe reaction mixture is heated to 165°-170° for 75 minutes
  5. temperatureThe mixture is then cooled to 90°
  6. stirringThe resulting mixture is stirred for one hour
  7. customthe layers are separated
  8. washthe benzene layer is washed with water
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-c531ef34e80042bb9180330548577505
Source dataset
uspto-grants-1976_08
Patent number
US03976633

Reaction notes

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