Ethyl (3-nitrophenyl)acetate → Ethyl 2-(3-aminophenyl)acetate

HRID 1930316Notes

Reaction equation

HRID 1930316 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 14997011Ethyl (3-nitrophenyl)acetate

Product 1

HCID 13042040Ethyl 2-(3-aminophenyl)acetateYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of ethyl 2-(3-nitrophenyl)acetate (12 g, 57.4 mmol) and Pd/C (1.2 g, 10%) in methanol (100 mL) was hydrogenated (45 psi) at RT for 12 h. The mixture was filtered and the filtrate was concentrated to afford ethyl 2-(3-aminophenyl)acetate (10 g, 97% yield). 1H NMR (400 MHz, DMSO-d6): δ 6.91 (t, J=1.6 Hz, 1 H), 6.42-6.40 (m, 2 H), 6.35 (d, J=7.6 Hz, 1 H), 5.00 (s, 2 H), 4.03 (q, J=7.2 Hz, 2 H), 3.41 (s, 2 H), 1.15 (t, J=7.2 Hz, 3 H).

Workup

  1. customat RT
  2. customfor 12 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9a42374893334306bb2850fde581e492
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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