(4-Nitrophenyl)(pyrrolidin-1-yl)methanone → 4-(Pyrrolidin-1-ylcarbonyl)aniline

HRID 546615Notes

Reaction equation

HRID 546615 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[N:10]1([C:8]([C:7]2[CH:15]=[CH:16][C:4]([NH2:1])=[CH:5][CH:6]=2)=[O:9])[CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 386112(4-Nitrophenyl)(pyrrolidin-1-yl)methanoneHCID 2723923Ammonium formate

Product 1

HCID 5778004-(Pyrrolidin-1-ylcarbonyl)anilineYield 115.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1.28 g of 1-(4-nitrobenzoyl)pyrrolidine obtained in stage a) below in 50 mL of methanol are added, under argon, 4.26 g of ammonium formate and 9 mg of 10% palladium-on-charcoal. The reaction mixture is stirred at room temperature for 5 hours and then filtered through Celite and concentrated under reduced pressure. The residue is taken up in water and extracted with ethyl acetate. The organic phase is then washed with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure to give 1.28 g of 4-(pyrrolidin-1-ylcarbonyl)aniline, the characteristics of which are as follows:

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is then washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-976bb117e69147dfb22da00f6c7266ef
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

Loading…