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

HRID 2375753Notes

Reaction equation

HRID 2375753 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-fb60a897a6e749d681644c3028839bab
Source dataset
uspto-grants-2008_12
Patent number
US07465809B2

Reaction notes

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