Methyl 2-methoxy-2-(4-nitrophenyl)acetate → Methyl 2-(4-aminophenyl)-2-methoxyacetate

HRID 56523Notes

Reaction equation

HRID 56523 reaction equation
[CH3:1][O:2][CH:3]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)[C:4]([O:6][CH3:7])=[O:5]>CCO.CCOC(C)=O.[Pd]>[NH2:14][C:11]1[CH:10]=[CH:9][C:8]([CH:3]([O:2][CH3:1])[C:4]([O:6][CH3:7])=[O:5])=[CH:13][CH:12]=1

Participants

5

Reactant 1

HCID 10105072Methyl 2-methoxy-2-(4-nitrophenyl)acetate

Product 1

HCID 58431984Methyl 2-(4-aminophenyl)-2-methoxyacetateYield 77%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 2-methoxy-2-(4-nitrophenyl)acetate (0.42 g, 1.87 mmol) in absolute EtOH (15 mL) was degassed by alternately putting under house vacuum and argon three times for several minutes each then 10% Pd/C (0.19 g) was added. The mixture was stirred under H2 (1 atm.) for 3 hrs then diluted with EtOAc and filtered through a pad of Celite and silica gel. The filtrate was concentrated in vacuo. Purification by chromatography (25-40% EtOAc-hexanes) provided methyl 2-(4-aminophenyl)-2-methoxyacetate as a yellow oil containing impurities (0.6 g from two batches, 77% yield). The compound was used without further purification.

Workup

  1. waitby alternately putting under house vacuum and argon three times for several minutes
  2. filtrationfiltered through a pad of Celite and silica gel
  3. concentrationThe filtrate was concentrated in vacuo
  4. customPurification by chromatography (25-40% EtOAc-hexanes)

Sources & evidence

ORD record
ord-dfc19011428c4bb6a7eb37d1c66b623c
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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