Methyl (4-nitrophenoxy)acetate → Methyl(4-aminophenoxy)acetate

HRID 1458689Notes

Reaction equation

HRID 1458689 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[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][CH3:13])=[O:11])=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 700522Methyl (4-nitrophenoxy)acetate

Product 1

HCID 6422115Methyl(4-aminophenoxy)acetateYield 94.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 4-nitrophenoxyacetate (5.0 g; 24 mmol) was dissolved in 150 ml of methanol in a reactor, followed by the addition of 480 mg of 5% Pd/C. The reactor was purged with nitrogen gas. Under a hydrogen gas atmosphere, the resultant mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reactor was purged again with nitrogen gas. The Pd/C was filtered off and the solvent was then distilled out under reduced pressure, whereby 4.1 g of a brown oil were obtained (yield: 92%).

Workup

  1. customThe reactor was purged with nitrogen gas
  2. customAfter completion of the reaction
  3. customthe reactor was purged again with nitrogen gas
  4. filtrationThe Pd/C was filtered off
  5. distillationthe solvent was then distilled out under reduced pressure

Sources & evidence

ORD record
ord-55b52cd3a6554cd182cc196c401ea283
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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