Tert-butyl 2-(4-nitrophenoxy)acetate → Tert-butyl 2-(4-aminophenoxy)acetate

HRID 1778241Notes

Reaction equation

HRID 1778241 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 22061043Tert-butyl 2-(4-nitrophenoxy)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 22060435Tert-butyl 2-(4-aminophenoxy)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a 100-mL round-bottom flask, was placed tert-butyl 2-(4-nitrophenoxy)acetate (2 g, 7.74 mmol, 1.00 equip, 98%), Palladium on carbon (200 mg), and methanol (50 mL). To the above hydrogen was introduced. The resulting solution was stirred for 18 h at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10) to yield tert-butyl 2-(4-aminophenoxy)acetate as a reddish oil.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-4116e8a6e3544f46b9830db3340d5b66
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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