Trifluoroacetic acid → 2-Amino-6-(trifluoromethyl)benzonitrile

HRID 711753Notes

Reaction equation

HRID 711753 reaction equation
COC1C=CC(C[NH:8][C:9]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[C:10]=2[C:11]#[N:12])=CC=1.FC(F)(F)C(O)=O>>[NH2:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[C:10]=1[C:11]#[N:12]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 673999202-(4-Methoxybenzylamino)-6-(trifluoromethyl)benzonitrile

Product 1

HCID 226251952-Amino-6-(trifluoromethyl)benzonitrileYield 99.9%

Procedure

2-(4-Methoxybenzylamino)-6-(trifluoromethyl)benzonitrile (Example 144c) (3.49 g, 11.4 mmol) was treated with trifluoroacetic acid (TFA) (35 mL) at 0° C., and then stirred at room temperature for 20 min. The TFA was removed under vacuum, and the residue was dissolved in CH2Cl2 (150 mL) and washed with 1M NaOH. The organic layer was dried with MgSO4, filtered and removed under vacuum. The crude product was purified by chromatography on silica gel eluting with CH2Cl2 to give 2.12 g (99%) 2-amino-6-(trifluoromethyl)benzonitrile as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.45 (m, 1H), 7.07 (m, 1H), 6.96 (m, 1H), 6.60 (br s, 2H).

Workup

  1. customThe TFA was removed under vacuum
  2. dissolutionthe residue was dissolved in CH2Cl2 (150 mL)
  3. washwashed with 1M NaOH
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. customremoved under vacuum
  7. customThe crude product was purified by chromatography on silica gel eluting with CH2Cl2

Sources & evidence

ORD record
ord-0c749e272b7a4362958563738ed9e854
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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