HCID 58307276, compound → 927672-74-0

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][C:14]=1[N+:15]([O-])=O)[O:6][CH2:7][CH2:8][N:9]([CH3:11])[CH3:10].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:10][N:9]([CH3:11])[CH2:8][CH2:7][O:6][C:5]1[CH:12]=[CH:13][C:14]([NH2:15])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

Procedure

A mixture of [2-(3-Methoxy-4-nitrophenoxy)ethyl]dimethylamine (1.0 g, 4.2 mmol) and 5% Pd—C (0.2 g) in ethyl acetate (75 mL) was shaken under 50 psi of hydrogen for 24 hours. The mixture was filtered through Celite and evaporated, providing 0.80 g of the product as a light gold oil, in 91% yield: 1H NMR (CDCl3) δ 2.33 (s, 6H), 2.69 (t, J=5.8 Hz, 2H), 3.82 (s, 3H), 4.00 (t, J=5.8 Hz, 2H), 6.35 (dd, J=8.3 Hz, J=2.6 Hz, 1H), 6.50 (d, J=2.6 Hz, 1H), 6.63 (d, J=8.3 Hz, 1H).