[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:16])[CH2:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[C:5]([N+:17]([O-])=O)[CH:4]=1)#[CH:2].CCO.Cl>[Fe].C1COCC1>[CH3:15][N:13]([CH3:14])[CH2:12][CH2:11][CH2:10][N:9]([CH3:16])[C:6]1[C:5]([NH2:17])=[CH:4][C:3]([C:1]#[CH:2])=[CH:8][CH:7]=1To N-(4-ethynyl-2-nitro-phenyl)-N,N′,N′-trimethyl-propane-1,3-diamine (730 mg, 2.79 mmol), EtOH (40 mL) and THF (13 mL) was added concentrated HCl (1.0 mL) and iron metal (10.6 g, 191 mmol). A reflux condenser was attached and the mixture was heated overnight at 90° C. The cooled mixture was filtered through a pad of Celite, concentrated and purified by flash chromatography (90:10:1 CH2Cl2/MeOH/NH4OH) to yield N1-(3-dimethylamino-propyl)-4-ethynyl-N1-methyl-benzene-1,2-diamine. MS m/z=232 [M+1]+. Calc'd for C14H21N3: 231.34.
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