HCID 86660198, compound → HCID 70098420, compound

HRID 467786Notes

Reaction equation

HRID 467786 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]=[CH:9][C:10]=1[N+:11]([O-])=O)=[O:4]>C(O)C.[Pd]>[NH2:11][C:10]1[CH:9]=[CH:8][C:7]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:6][C:5]=1[C:3](=[O:4])[NH:2][CH3:1]

Participants

4

Reactant 1

HCID 86660198HCID 86660198, compound

Product 1

HCID 70098420HCID 70098420, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of (E)-ethyl 3-(3-(methylcarbamoyl)-4-nitrophenyl)acrylate (345 mg, 1.24 mmol) in ethanol (10 ml) at r.t. under an argon atmosphere was added 10% Pd/C (52.8 mg, 496 μmol). The black suspension was hydrogenated at normal pressure and r.t. overnight. The catalyst was removed by filtration. The filtrate was concentrated. The crude product was purified by silica gel chromatography using a methylenchloride/MeOH gradient to give the title compound (175 mg, 57%) as white solid.

Workup

  1. customwas hydrogenated at normal pressure and r.t. overnight
  2. customThe catalyst was removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b4e531ac2de94f1bb1ec8fe0a22d147a
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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