2-(3-Chloro-2,2,3-trifluoro-propionamido)-5-nitrophenol → 2-(3-Chloro-2,2,3-trifluoropropionamido)-5-aminophenol

HRID 1759585Notes

Reaction equation

HRID 1759585 reaction equation
[Cl:1][CH:2]([F:19])[C:3]([F:18])([F:17])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[OH:16])=[O:5].[H][H]>[Ni].C(O)C>[Cl:1][CH:2]([F:19])[C:3]([F:17])([F:18])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[OH:16])=[O:5]

Participants

5

Reactant 2

HCID 205313262-(3-Chloro-2,2,3-trifluoro-propionamido)-5-nitrophenolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 205313242-(3-Chloro-2,2,3-trifluoropropionamido)-5-aminophenol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

In an autoclave 267 g (0.895 mole) of compound (b), 18 ml of Raney-nickel suspension, and 1.3 l of ethanol were placed. The nitro group was reduced with hydrogen at a temperature of 65°-70° C. and an initial pressure of 100-105 bar. After 90 min the required amount of hydrogen had been taken up. The solution was let off and after filtering of the Raney nickel concentrated by evaporation. The dry residue was dissolved in 310 ml of boiling methanol, filtered, and diluted with 360 ml of water.

Workup

  1. filtrationafter filtering of the Raney nickel
  2. concentrationconcentrated by evaporation
  3. dissolutionThe dry residue was dissolved in 310 ml of boiling methanol
  4. filtrationfiltered
  5. additiondiluted with 360 ml of water

Sources & evidence

ORD record
ord-7cb2bce5d3eb4fac93fe4cd899310e6a
Source dataset
uspto-grants-1982_07
Patent number
US04341864

Reaction notes

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