N-(4-Cyano-3-fluoro-2-methylphenyl)acetamide → 4-Amino-2-fluoro-3-methylbenzonitrile

HRID 501633Notes

Reaction equation

HRID 501633 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9]C(=O)C)=[C:5]([CH3:13])[C:4]=1[F:14])#[N:2]>Cl.CCO>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:14])[C:5]=1[CH3:13]

Participants

3

Reactant 1

HCID 68454968N-(4-Cyano-3-fluoro-2-methylphenyl)acetamide

Product 1

HCID 450786764-Amino-2-fluoro-3-methylbenzonitrileYield 96.8%

Reagents, catalysts & solvents 1

HCID 21887872Ethanol hydrochlorideSolvent

Procedure

N-(4-cyano-3-fluoro-2-methyl-phenyl)-acetamide (72C) (450 mg, 2.34 mmol) was dissolved in 1:1 conc. HCl/EtOH (20 mL), and the mixture was refluxed for 1 h. The reaction was cooled to rt and concentrated. The residue was dissolved in EtOAc (30 mL), washed with sat. aq. NaHCO3 and brine, dried (MgSO4), filtered and concentrated. The residue was recrystallized from EtOAc/Hexane to provide the title compound (340 mg). LC/MS: m/z 151 [M+H]+

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc (30 mL)
  4. washwashed with sat. aq. NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was recrystallized from EtOAc/Hexane

Sources & evidence

ORD record
ord-16656997c5c44c3e941ebff13ef073e5
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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