Hydrochloric Acid → 1-[4-fluoro-2-(methylsulfonyl)phenyl]methanaminium Chloride

HRID 897363Notes

Reaction equation

HRID 897363 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:3]=1.[ClH:14]>[Pd].C(O)C>[Cl-:14].[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH3+:7])=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 167539464-Fluoro-2-(methylsulfonyl)benzonitrile

Product 1

HCID 223464531-[4-fluoro-2-(methylsulfonyl)phenyl]methanaminium Chloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-fluoro-2-(methylsulfonyl)benzonitrile (5.6 g, 28.11 mmol) was added to a dry Parr bottle. Ethanol (50 mL) and conc HCl (10 mL) were added and the reaction solution put under an Argon atmosphere. 10% Pd/C (1 gram) was added and the reaction vessel placed on a Parr hydrogenation apparatus. The reaction was placed under an atmosphere of H2 (50 psi) and shaken overnight. After overnight the ratio of starting material to product was 50:50. The reaction was filtered through celite and concentrated slightly. Conc. HCl (10 mL) and 10% Pd/C (1 gram) were added and the reaction was again put under H2 (50 psi). The reaction was again shaken overnight. The crude reaction was filtered through celite and concentrated to afford the desired material as a white solid.

Workup

  1. waitAfter overnight the ratio of starting material to product was
  2. filtrationThe reaction was filtered through celite
  3. concentrationconcentrated slightly
  4. additionConc. HCl (10 mL) and 10% Pd/C (1 gram) were added
  5. waitThe reaction was again shaken overnight
  6. customThe crude reaction
  7. filtrationwas filtered through celite
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0b169d7e3f1d48c9a282010f22e44636
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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