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

HRID 1003239Notes

Reaction equation

HRID 1003239 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 12433959Ethyl 4-(2-nitrophenoxy)butanoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11816929Ethyl 4-(2-aminophenoxy)butanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3) (1.27 g, 5.0 mM) in 15 mL ethyl acetate containing 200 mg of 5% palladium on carbon is reacted in a hydrogen atmosphere (40 psig.) at room temperature until hydrogen uptake ceases. The mixture is then filtered and concentrated in vacuo to yield 1.0+ g of (4) as an oil/low melting solid.

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b9a4e4c02504718852514f05c2d3592
Source dataset
uspto-grants-2000_04
Patent number
US06046183

Reaction notes

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