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

HRID 241747Notes

Reaction equation

HRID 241747 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-2da470e3f7c74a7fb72a30e9026f1529
Source dataset
uspto-grants-2014_02
Patent number
US08653073B2

Reaction notes

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