2-Nitro-4-(trifluoromethyl)benzonitrile → 2-Amino-4-(trifluoromethyl)benzonitrile

HRID 1644681Notes

Reaction equation

HRID 1644681 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O>C(O)(=O)C.[Zn]>[NH2:1][C:4]1[CH:11]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

4

Reactant 1

HCID 699022-Nitro-4-(trifluoromethyl)benzonitrile

Product 1

HCID 134390282-Amino-4-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc dust (30 g) was added in portions to a 5° C. solution of 2-nitro-4-trifluoromethyl-benzonitrile (3.0 g, 14 mmol) in glacial acetic acid (260 mL). The reaction mixture was allowed to warm to room temperature, then stirred at room temperature for 1 hour. The reaction mixture was filtered through a celite plug, and the celite layer was washed with glacial acetic acid. The combined filtrate and washings were concentrated to afford 2-amino-4-trifluoromethyl-benzonitrile as an oily, orange solid which was used in subsequent reactions without additional purification.

Workup

  1. filtrationThe reaction mixture was filtered through a celite plug
  2. washthe celite layer was washed with glacial acetic acid
  3. concentrationThe combined filtrate and washings were concentrated

Sources & evidence

ORD record
ord-a98049f3d5f2496abb2ae0bf8077d406
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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