Ethyl 2-(4-nitrophenoxy)acetate → Ethyl 2-(4-aminophenoxy)acetate

HRID 1482703Notes

Reaction equation

HRID 1482703 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 308938Ethyl 2-(4-nitrophenoxy)acetate

Product 1

HCID 412616Ethyl 2-(4-aminophenoxy)acetateYield 76.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of Pd/C (0.5 g) in methanol (10 mL), ethyl 2-(4-nitrophenoxy)acetate (1.5 g) was added under nitrogen atmosphere into the 50 mL 3-neck RBF at room temperature. Hydrogen gas was bubbled through the reaction for 2 hr at room temperature. The reaction was monitored on TLC using CHCl3:methanol (9.5:0.5) as mobile phase. After completion of the reaction, the mixture was filtered using Celite and the filter cake was washed with methanol. The filtrate was concentrated under reduced pressure at 40° C. to give 1.0 g of ethyl 2-(4-aminophenoxy)acetate as a brown solid.

Workup

  1. additionwas added under nitrogen atmosphere into the 50 mL 3-neck RBF at room temperature
  2. customHydrogen gas was bubbled through the reaction for 2 hr at room temperature
  3. customAfter completion of the reaction
  4. filtrationthe mixture was filtered
  5. washthe filter cake was washed with methanol
  6. concentrationThe filtrate was concentrated under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-d30603c1a29e4b20a3485dbddf89e4b9
Source dataset
uspto-grants-2016_08
Patent number
US09415049B2

Reaction notes

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