Ethanol → p-Phenetidine, 3-methoxy-

HRID 2374176Notes

Reaction equation

HRID 2374176 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[O:13][CH3:14])[CH3:2].CCO>[Pd].CCOC(C)=O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[O:13][CH3:14])[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 21829131HCID 21829131, compound

Product 1

HCID 209360p-Phenetidine, 3-methoxy-Yield 103.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-ethoxy-5-nitroanisole from Step 1 (5.50 g, 27.9 mmol) and 10% Pd/C (1.0 g) in 1:1 EtOH:EtOAc (50 ml) was shaken under an atmosphere of H2 (35-40 psi) for 30 min. The reaction mixture was filtered through Celite and concentrated under vacuum to afford 4-ethoxy-3-methoxyaniline (4.82 g, 100%) as a brown solid: mp 54-56° C. 1H NMR (DMSO-d6) δ 6.61 (d, 1H), 6.25 (d, 1H), 6.03 (dd, 1H), 4.65 (s, 2H), 3.82 (q, 2H), 3.66 (s, 3H), 1.22 (t, 3H); 13C NMR (DMSO-d6) δ 143.6, 138.8, 116.6, 105.1, 99.9, 65.0, 55.1, 15.1; MS (ESI+) for m/z 168 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5ce0ef523237468197618cc8a49c6141
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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