Hydrochloric Acid → 4-Amino-5-fluoro-2-(trifluoromethyl)benzonitrile

HRID 1504945Notes

Reaction equation

HRID 1504945 reaction equation
[C:1]([C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][C:6]([NH:13]C(=O)C)=[C:5]([F:17])[CH:4]=1)#[N:2].Cl>CCO>[NH2:13][C:6]1[C:5]([F:17])=[CH:4][C:3]([C:1]#[N:2])=[C:8]([C:9]([F:12])([F:10])[F:11])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68292028N-(4-cyano-2-fluoro-5-(trifluoromethyl)phenyl)acetamide

Product 1

HCID 682929284-Amino-5-fluoro-2-(trifluoromethyl)benzonitrileYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of compound 24 (800 mg, 3.25 mmol) in EtOH (10 mL) was added concentrated HCl solution (12N, 5 mL). The mixture was heated at reflux for 1 h, cooled to room temperature, concentrated in vacuo. The resulting white solid was dissolved in EtOAc, washed with saturated aqueous NaHCO3, dried over Na2SO4 and concentrated to give compound 25 (660 mg, 99%) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ7.40 (d, 1H, J=7.2 Hz), 7.09 (d, 1H, J=10.0 Hz), 4.48 (br s, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resulting white solid was dissolved in EtOAc
  5. washwashed with saturated aqueous NaHCO3
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0280bbb772fb42539330de233add3d48
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

Loading…