Methane → HCID 14665031, compound

HRID 845178Notes

Reaction equation

HRID 845178 reaction equation
[Cl:1][CH:2]([F:24])[C:3]([F:23])([F:22])[O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]=NC2C=CC([N+]([O-])=O)=CC=2)=[N:9][CH:10]=1.C.[H][H]>C(O)(=O)C.[Pd]>[NH2:11][C:8]1[CH:7]=[CH:6][C:5]([O:4][C:3]([F:23])([F:22])[CH:2]([Cl:1])[F:24])=[CH:10][N:9]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 14665027HCID 14665027, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14665031HCID 14665031, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

In a 1 liter VA stainless steel autoclave, 85.1 g (0.24 mol) of 5-(2-chloro-1,1,2-trifluoroethoxy)-2-(4-nitrophenylazo)pyridine were hydrogenated in 600 ml of acetic acid, with addition of 10 g of palladium (10%) on activated charcoal, using 61 bar (take-up) of hydrogen at 20°-25° C. The mixture was filtered and the solvent removed by distillation on a rotary evaporator. The residue was taken up in 500 ml of dichloromethane, washed with 100 ml of 20% strength aqueous sodium carbonate and four times with 100 ml of water in each case, and dried over sodium sulfate. The solvent was subsequently removed by evaporation on a rotary evaporator and the residue was distilled in a high vacuum.

Workup

  1. customat 20°-25° C
  2. filtrationThe mixture was filtered
  3. customthe solvent removed by distillation on a rotary evaporator
  4. washwashed with 100 ml of 20% strength aqueous sodium carbonate and four times with 100 ml of water in each case
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was subsequently removed by evaporation on a rotary evaporator
  7. distillationthe residue was distilled in a high vacuum

Sources & evidence

ORD record
ord-a67407684cb141b79f850ab537e70b86
Source dataset
uspto-grants-1988_07
Patent number
US04756739

Reaction notes

Loading…