Tetrahydrofuran → HCID 68207886, compound

HRID 1025407Notes

Reaction equation

HRID 1025407 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-])=O.C1COCC1>[Pd].CN(C)C=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 10636688HCID 10636688, compound

Product 1

HCID 68207886HCID 68207886, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 48.8 g of methyl 4-[(E)-2-(4-nitrophenyl)vinyl]benzoate, 600 mL of THF, and 200 mL of N,N-dimethylformamide (DMF) was added 10.0 g of 10% palladium on carbon (wetted with 55% H2O), followed by stirring at room temperature for 8 hours under a hydrogen atmosphere (1 atm). The inside of the reaction container was replaced with argon, and then the insoluble materials were filtered off on a celite layer. The filtrate was concentrated under reduced pressure, and to the residue was added 1000 mL of water, followed by stirring at room temperature for 30 minutes. The precipitate was collected by filtration to obtain 43.3 g of methyl 4-[2-(4-aminophenyl)ethyl]benzoate as a white solid.

Workup

  1. filtrationthe insoluble materials were filtered off on a celite layer
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additionto the residue was added 1000 mL of water
  4. stirringby stirring at room temperature for 30 minutes
  5. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-118438dd59ed47bdab4382e3b9563a6e
Source dataset
uspto-grants-2014_05
Patent number
US08729068B2

Reaction notes

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