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

HRID 76445

Reaction equation

HRID 76445 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>CCO.[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)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 4-nitrophenoxyacetate (15 g) in EtOH (400 mL) was hydrogenated at 40 PSI for 40 minutes in the presence of 10% Pd/C (1.5 g, 10% by weight). After the filtration through a celite the solvent was removed under a reduced pressure to obtain ethyl 4-aminophenoxyacetate. 1H NMR (CDCl3): δ 6.77 (d, 2H, 8.1 Hz), 6.60 (d, 2H, J=8.0 Hz), 4.50 (s, 2H), 4.24 (q, 2H), 1.24 (t, 3H); LCMS: ret. time: 12.00 min.; purity: 100%; MS (m/e): 196 (MH+).

Workup

  1. filtrationAfter the filtration through a celite the solvent
  2. customwas removed under a reduced pressure

Sources & evidence

ORD record
ord-872e1e5d7c4f4041bb690e65f439b6a1
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Linked notes

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