HCID 19789261, compound → HCID 59250076, compound

HRID 2068732Notes

Reaction equation

HRID 2068732 reaction equation
[F:1][C:2]1[C:3]([N+:15]([O-])=O)=[CH:4][C:5]([N+:12]([O-])=O)=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1.[H][H]>CO.[Pd]>[NH2:12][C:5]1[CH:4]=[C:3]([NH2:15])[C:2]([F:1])=[CH:7][C:6]=1[CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 19789261HCID 19789261, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59250076HCID 59250076, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(5-Fluoro-2,4-dinitro-phenyl)-acetic acid 9b (10 g, 38.7 mmol) was dissolved in 150 mL of methanol under stirring at room temperature, and palladium on activated carbon (5%, 1.5 g) was then added to the solution. The reaction mixture was hydrogenated under 0.3 Mpa of hydrogen. The reaction was completed until TLC showed the disappearance of starting materials. The above mixture was filtered twice and the filtrate was concentrated under reduced pressure to give the title compound (2,4-diamino-5-fluoro-phenyl)-acetic acid 9c (7.12 g) as a brown solid which was directly used in the further reaction.

Workup

  1. filtrationThe above mixture was filtered twice
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-580dce28ddf4452fa73bf5cd609a93c4
Source dataset
uspto-grants-2012_10
Patent number
US08299069B2

Reaction notes

Loading…