HCID 12454244, compound → HCID 39235406, compound

HRID 230556Notes

Reaction equation

HRID 230556 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-])=O.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:9])[CH3:10])=[CH:4][C:3]=1[NH2:11]

Participants

5

Reactant 2

HCID 12454244HCID 12454244, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 39235406HCID 39235406, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.23 g (17.54 mmol) of (4-fluoro-3-nitrophenyl)-dimethylamine are added, at a temperature in the region of 20° C., to a suspension of 0.6 g (5.63 mmol) of 10% palladium-on-charcoal in 100 cm3 of methanol. After hydrogenation for 30 minutes in an autoclave under 5 bar of hydrogen, at a temperature in the, region of 25° C., the reaction mixture is filtered, the catalyst is rinsed with 3 times 10 cm3 of methanol, and the filtrate is then concentrated to dryness under reduced pressure (2.7 kPa), to give 2.7 g of 4-fluoro-N1,N1-dimethylbenzene-1,3-diamine, in the form of a brown oil;

Workup

  1. filtrationat a temperature in the, region of 25° C., the reaction mixture is filtered
  2. washthe catalyst is rinsed with 3 times 10 cm3 of methanol
  3. concentrationthe filtrate is then concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-3bc74c3fd9d44167877c4fccf6466c62
Source dataset
uspto-grants-2009_07
Patent number
US07566736B2

Reaction notes

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