3-[2-(4-Nitro-phenyl)-ethyl]-oxazolidin-2-one → 3-(2-(4-Aminophenyl)ethyl)-1,3-oxazolidin-2-one

HRID 44295Notes

Reaction equation

HRID 44295 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][O:14][C:13]2=[O:17])=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][O:14][C:13]2=[O:17])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 107761683-[2-(4-Nitro-phenyl)-ethyl]-oxazolidin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 107034763-(2-(4-Aminophenyl)ethyl)-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C 10% (500 mg) is added to a solution of the compound obtained in Step B (16.6 mmoles) in MeOH (100 ml). The reaction mixture is stirred at 50° C. under 4.5 bars of hydrogen for 4 hours. The catalyst is filtered off and then washed with MeOH. The filtrate is evaporated to dryness and the product obtained is triturated in 10 ml of MeOH. The solid obtained is filtered off and dried in vacuo at 40° C. overnight to yield the title product in the form of a white solid, which is used directly in the next Step.

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with MeOH
  3. customThe filtrate is evaporated to dryness
  4. customthe product obtained
  5. customis triturated in 10 ml of MeOH
  6. customThe solid obtained
  7. filtrationis filtered off
  8. customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-3b9be956c013464f9262d597b2d2fc5d
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

Loading…