5-(3-Dimethylaminopropoxy)-4-fluoro-2-nitrophenylamine → 4-(3-Dimethylaminopropoxy)-5-fluorobenzene-1,2-diamine

HRID 2243378Notes

Reaction equation

HRID 2243378 reaction equation
[H][H].[CH3:3][N:4]([CH3:20])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[C:10]([F:19])=[CH:11][C:12]([N+:16]([O-])=O)=[C:13]([NH2:15])[CH:14]=1>C(O)C.[Pd]>[CH3:20][N:4]([CH3:3])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([NH2:15])[C:12]([NH2:16])=[CH:11][C:10]=1[F:19]

Participants

5

Reactant 2

HCID 578128495-(3-Dimethylaminopropoxy)-4-fluoro-2-nitrophenylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 578128554-(3-Dimethylaminopropoxy)-5-fluorobenzene-1,2-diamineYield 90.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 25 ml autoclave, dissolve 350 mg of 5-(3-dimethylaminopropoxy)-4-fluoro-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 123 ml. After filtration of the catalyst and then concentration to dryness under reduced pressure, we obtain 280 mg of 4-(3-dimethylaminopropoxy)-5-fluorobenzene-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-ebe79418417a4df28c28ca27d1d4ef58
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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