HCID 86660198, compound → HCID 70098420, compound

HRID 2368383Notes

Reaction equation

HRID 2368383 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-1245ccc3e2854f3784604f3954eeb8e7
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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