HCID 89648988, compound → HCID 89649651, compound

HRID 530267Notes

Reaction equation

HRID 530267 reaction equation
[F:1][C:2]([F:24])([O:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([N+:18]([O-])=O)=[CH:13][C:12]=1[N+:21]([O-])=O)[C:3]([N:5]([CH2:8][CH3:9])[CH2:6][CH3:7])=[O:4]>CO.[Pd]>[F:24][C:2]([F:1])([O:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([NH2:18])=[CH:13][C:12]=1[NH2:21])[C:3]([N:5]([CH2:6][CH3:7])[CH2:8][CH3:9])=[O:4]

Participants

4

Reactant 1

HCID 89648988HCID 89648988, compound

Product 1

HCID 89649651HCID 89649651, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2,2-difluoro-2-(2,4-dinitro-5-fluoro-phenoxy)-N,N-diethyl-acetamide (13.5 g, 38.4 mmol) and Pd/C (10% Pd, dry catalyst, 2.0 g, 1.9 mmol) in MeOH (395) was stirred under an atmosphere of hydrogen (pressure of 0.1 bar) at 50° C. for 2 h. After completion of the reaction the pressure was released, the catalyst was filtered off and the filtrate was evaporated to dryness. The product was purified by column chromatography (SiO2, cyclohexane/EtOAc mixtures). The product was obtained as an off-white solid (11.0 g, 88% pure by NMR, 33.2 mmol, 86% yield).

Workup

  1. customAfter completion of the reaction the pressure
  2. filtrationthe catalyst was filtered off
  3. customthe filtrate was evaporated to dryness
  4. customThe product was purified by column chromatography (SiO2, cyclohexane/EtOAc mixtures)
  5. customThe product was obtained as an off-white solid (11.0 g, 88% pure by NMR, 33.2 mmol, 86% yield)

Sources & evidence

ORD record
ord-8c97e5ad26bc403d96e3b893295b931c
Source dataset
uspto-grants-2016_05
Patent number
US09353070B2

Reaction notes

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