Methanol → 3-methoxy-N1-(3-methoxypropyl)benzene-1,2-diamine

Reaction equation

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

Participants

Procedure

Into a 100 mL round bottomed flask was added 3-methoxy-N-(3-methoxypropyl)-2-nitroaniline (36A) (560 mg, 2.33 mmol) and methanol (46 mL). Zinc metal (2.11 g, 32.4 mmol) and acetic acid (2.0 mL) was added and the mixture was stirred at room temperature for 5 hr. The mixture was filtered through a fritted Buchner funnel and the solvent was removed under vacuum. Ethyl acetate (100 mL) was added and the precipitate was filtered through a Buchner funnel with a pad of Celite. The filtrate was concentrated under vacuum to leave 3-methoxy-N1-(3-methoxypropyl)benzene-1,2-diamine (37B) as a yellow oil which was used without further purification. ESI-MS:mlz 211.4 (M-F1-1)+.