HCID 86646932, compound → HCID 68512324, compound

HRID 1929338Notes

Reaction equation

HRID 1929338 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([N+:22]([O-])=O)[CH:14]=1)[CH3:11].[H][H]>C(O)C.[Pt]=O>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[CH:14]=[C:15]([NH2:22])[C:16]([NH2:19])=[CH:17][CH:18]=1)[CH3:11]

Participants

5

Reactant 2

HCID 86646932HCID 86646932, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68512324HCID 68512324, compoundYield 62.7%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent2×

Procedure

In an autoclave, cover 36 mg of platinum oxide with 5 cm3 of ethanol; add a solution of 600 mg of 4-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-1,2-dinitrobenzene in 67 cm3 of ethanol. This mixture is hydrogenated under 200 kPa of hydrogen and at a temperature close to 20° C. After reaction for about twenty hours, the mixture is filtered and concentrated under vacuum under reduced pressure (0.2 kPa). After filtration on silica [eluent: dichloromethane/methanol (98/2 by volume)], we obtain 316 mg of 4-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]benzene-1,2-diamine in the form of a brown resin, which has the following characteristics:

Workup

  1. customclose to 20° C
  2. customAfter reaction for about twenty hours
  3. filtrationthe mixture is filtered
  4. concentrationconcentrated under vacuum under reduced pressure (0.2 kPa)
  5. filtrationAfter filtration on silica [eluent: dichloromethane/methanol (98/2 by volume)], we

Sources & evidence

ORD record
ord-70effe7e6a724076b340b22ad902a281
Source dataset
uspto-grants-2012_05
Patent number
US08188078B2

Reaction notes

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