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

HRID 1179317Notes

Reaction equation

HRID 1179317 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].CO>[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 887MethanolSolvent

Procedure

4-fluoro-2-(methylsulfonyl)benzonitrile (5.6 g, 28.11 mmol) was added to a dry Parr bottle. Methanol (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-8292c132be2a47508c119d4edf076c11
Source dataset
uspto-grants-2007_10
Patent number
US07279487B2

Reaction notes

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