HCID 14855594, compound → HCID 14855595, compound

HRID 477411Notes

Reaction equation

HRID 477411 reaction equation
[F:1][C:2]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:17]=2[F:25])[CH:12]=[CH:11][C:3]=1[O:4][CH:5]([CH3:10])[C:6]([O:8][CH3:9])=[O:7]>C(O)C.[Pd]>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:13]2[CH:12]=[CH:11][C:3]([O:4][CH:5]([CH3:10])[C:6]([O:8][CH3:9])=[O:7])=[C:2]([F:1])[CH:14]=2)=[C:17]([F:25])[CH:18]=1

Participants

4

Reactant 1

HCID 14855594HCID 14855594, compound

Product 1

HCID 14855595HCID 14855595, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of methyl 2-(2-fluoro-4-(2-fluoro-4-nitrophenoxy)phenoxy)propanoate (6.5 g, 0.018 mole) in ethanol (150 ml) containing 5 percent palladium on charcoal (0.5 g) as catalyst was subjected to hydrogenation (initial pressure equals 50 psi) on a Parr apparatus. After 19 hours, the excess hydrogen was removed and nitrogen was bubbled through the liquid mixture. This mixture was filtered through celite and the ethanol removed by distillation. A slightly yellow oil weighting 5.8 grams (98 percent) resulted. NMR spectroscopy (1H, 19F) and infrared (I.R.) spectroscopy confirmed the structure as one being consistent with the desired product. It was used directly in the next step without further purification.

Workup

  1. customthe excess hydrogen was removed
  2. customnitrogen was bubbled through the liquid mixture
  3. filtrationThis mixture was filtered through celite
  4. customthe ethanol removed by distillation
  5. customA slightly yellow oil weighting 5.8 grams (98 percent) resulted

Sources & evidence

ORD record
ord-4e1965e0d3a84b6fbce03b91ef6d9981
Source dataset
uspto-grants-1989_12
Patent number
US04888050

Reaction notes

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