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

HRID 751148Notes

Reaction equation

HRID 751148 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-d2af42592c7c48aeba251318710da180
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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