(E)-methyl 3-[3-(methylcarbamoyl)phenyl]prop-2-enoate → Methyl 3-(3-(methylcarbamoyl)phenyl)propanoate

HRID 16911Notes

Reaction equation

HRID 16911 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7](/[CH:11]=[CH:12]/[C:13]([O:15][CH3:16])=[O:14])[CH:8]=[CH:9][CH:10]=1)=[O:4].[H][H]>[Pd].C(O)C.CN(C=O)C>[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

6

Reactant 2

HCID 66589796(E)-methyl 3-[3-(methylcarbamoyl)phenyl]prop-2-enoateHCID 178418361HCID 178418361, compound

Product 1

HCID 66589811Methyl 3-(3-(methylcarbamoyl)phenyl)propanoateYield 80.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (E)-methyl 3-[3-(methylcarbamoyl)phenyl]prop-2-enoate (3.77 g, 17.20 mmol) and 10% palladium on carbon (0.458 g, 0.43 mmol) in a mixture of ethanol (100 mL) and DMF (10.00 mL) was stirred at room temperature for 18 h under a balloon of hydrogen. The reaction mixture was filtered through celite and evaporated to dryness to afford methyl 3-(3-(methylcarbamoyl)phenyl)propanoate (3.05 g, 80%) as a white solid. MS: m/z 222 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-e15fcd6dc79b41feacd74cddc83b88cd
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

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