Water → HCID 19374371, compound

HRID 128523Notes

Reaction equation

HRID 128523 reaction equation
[Cl:1][C:2]1[C:3]([F:16])=[C:4]([C:8]([N+:13]([O-])=O)=[C:9]([F:12])[C:10]=1[F:11])[C:5]([OH:7])=[O:6].[H][H].O>[Ni].C(O)C>[NH2:13][C:8]1[C:9]([F:12])=[C:10]([F:11])[C:2]([Cl:1])=[C:3]([F:16])[C:4]=1[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 962WaterHCID 14896543HCID 14896543, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19374371HCID 19374371, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

63.9 g (0.25 mol) of 3-chloro-2,4,5-trifluoro-6-nitrobenzoic acid and 15 g of Raney nickel are suspended in 450 ml of ethanol. Hydrogenation is carried out at 10°-15° C. under a hydrogen pressure of 5-10 bar until the uptake of hydrogen has ended. The crude reaction mixture is poured onto 1 l of water. The carboxylic acid which has precipitated is dissolved by addition of 10% strength sodium hydroxide solution. When the catalyst has been filtered off with suction, a pH of 2-3 is established by addition of half-concentrated hydrochloric acid. The precipitate is filtered off with suction, washed with water and dried over KOH in a desiccator.

Workup

  1. customis carried out at 10°-15° C. under a hydrogen
  2. customThe crude reaction mixture
  3. customThe carboxylic acid which has precipitated
  4. dissolutionis dissolved by addition of 10% strength sodium hydroxide solution
  5. filtrationWhen the catalyst has been filtered off with suction
  6. additiona pH of 2-3 is established by addition of half-concentrated hydrochloric acid
  7. filtrationThe precipitate is filtered off with suction
  8. washwashed with water
  9. dry with materialdried over KOH in a desiccator

Sources & evidence

ORD record
ord-0a1ac9d476f24b8eba0f6dc3b7e41720
Source dataset
uspto-grants-1995_11
Patent number
US05464796

Reaction notes

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