4-Fluoro-5-(3-methoxypropoxy)-2-nitrophenylamine → 4-Fluoro-5-(3-methoxypropoxy)benzene-1,2-diamine

HRID 2243376Notes

Reaction equation

HRID 2243376 reaction equation
[H][H].[F:3][C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:8][C:7]([NH2:16])=[C:6]([N+:17]([O-])=O)[CH:5]=1>C(O)C.[Pd]>[F:3][C:4]1[CH:5]=[C:6]([NH2:17])[C:7]([NH2:16])=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15]

Participants

5

Reactant 2

HCID 673595584-Fluoro-5-(3-methoxypropoxy)-2-nitrophenylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 673605484-Fluoro-5-(3-methoxypropoxy)benzene-1,2-diamineYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 25 ml autoclave, dissolve 330 mg of 4-fluoro-5-(3-methoxypropoxy)-2-nitrophenylamine, obtained in the previous stage, in 20 ml of ethanol, add 40 mg of 10% palladium-on-charcoal and then subject to an initial hydrogen pressure of 1 bar at 20° C. for 16 hours. After cooling, the volume of hydrogen absorbed is 91 ml. After filtration of the catalyst and then concentration to dryness under reduced pressure, we obtain 290 mg of 4-fluoro-5-(3-methoxypropoxy)benzene-1,2-diamine, in the form of a viscous black oil, which is used as it is in the following stage, with the following characteristic:

Workup

  1. temperatureAfter cooling
  2. customthe volume of hydrogen absorbed
  3. filtrationAfter filtration of the catalyst
  4. concentrationconcentration to dryness under reduced pressure, we

Sources & evidence

ORD record
ord-1d090cc89da340c7b9ab44fe4d5da483
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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