HCID 10399255, compound → HCID 58861806, compound

HRID 1428802Notes

Reaction equation

HRID 1428802 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>CO.O1CCCC1.[Pd]>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:3][C:2]=1[CH3:1]

Participants

5

Reactant 1

HCID 10399255HCID 10399255, compound

Product 1

HCID 58861806HCID 58861806, compoundYield 90.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(3-methyl-4-nitrophenyl)propanoate (1.2 g, 5.05 mmol) was dissolved in methanol and tetrahydrofuran (1:1, 15 mL). 10% Pd/C (180 mg, 10%) was added to it. The resulting mixture was stirred at room temperature for 3 h under H2. TLC showed complete consumption of starting material. The mixture was filtered through celite bed and the filterate was concentrated under reduced pressure. The crude was purified by column chromatography to give ethyl 2-(4-amino-3-methylphenyl)propanoate (944 mg, 90%).

Workup

  1. customconsumption of starting material
  2. filtrationThe mixture was filtered through celite bed
  3. concentrationthe filterate was concentrated under reduced pressure
  4. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-b369e9764b4541899212ca122506d0f3
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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