4-Amino-5-iodo-2-(trifluoromethyl)benzonitrile → 4-Amino-5-cyano-2-trifluoromethyl-benzonitrile

HRID 505598Notes

Reaction equation

HRID 505598 reaction equation
[NH2:1][C:2]1[C:9](I)=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[C:15]([Cu])#[N:16]>CN1C(=O)CCC1>[NH2:1][C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[C:5]([C:6]#[N:7])=[CH:8][C:9]=1[C:15]#[N:16]

Participants

4

Reactant 2

HCID 250673774-Amino-5-iodo-2-(trifluoromethyl)benzonitrileHCID 178418546HCID 178418546, compound

Product 1

HCID 167568574-Amino-5-cyano-2-trifluoromethyl-benzonitrile

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-Amino-5-iodo-2-trifluoromethyl-benzonitrile (1.5 mmoL), CuCN (1.7 mmoL) in NMP (10 mL) was heated at 150° C. for 4 hrs. The reaction mixture was passed through a pad of Celite. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was washed with water, then brine, dried over anhydrous Na2SO4, filtered and concentrated to yield the title compound as a brown solid.

Workup

  1. customThe reaction mixture was then partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water
  3. dry with materialbrine, dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2615f75ca54b424db1ba6911fc79518e
Source dataset
uspto-grants-2010_08
Patent number
US07781473B2

Reaction notes

Loading…