Hydrazine hydrate (1:1) → 4,5-Bis(dodecyloxy)benzene-1,2-diamine

Reaction equation

[CH2:1]([O:13][C:14]1[CH:19]=[C:18]([N+:20]([O-])=O)[C:17]([N+:23]([O-])=O)=[CH:16][C:15]=1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O.NN>[Pd].C(O)C>[CH2:1]([O:13][C:14]1[CH:19]=[C:18]([NH2:20])[C:17]([NH2:23])=[CH:16][C:15]=1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

Procedure

This compound was synthesized according to a literature procedure.24 In a Schlenk tube, 1,2-Bis-dodecyloxy-4,5-dinitro benzene BK2—13 (2.36 g, 4.39 mmol), hydrazine monohydrate (8.25 ml, 48.5 mmol), 131 mg of Pd/C, and 65 ml of absolute ethanol were placed. The reaction mixture was refluxed under argon for 22 hours. Hot filtration under argon was then performed. Upon cooling, a white solid formed. The solid was washed with O2-free methanol and was dried overnight under nitrogen to yield 1.57 g (75%) of white solid. 1H (300 MHz, CDCl3) δ 6.353 (s, 2H), 3.880-3.835 (t, J=6.6 Hz, 4H), 3.062 (br s, 4H, NH2), 1.767-1.673 (pentet, J=7.2 Hz, 4H), 1.43-1.36 (m, 4H), 1.358-1.080 (m, 32H), 0.878-0.833 (t, J=7.2 Hz, 6H).13C (CDCl3, 75 MHz) δ 143.20, 128.20, 106.69, 70.67, 32.00, 29.78, 29.73, 29.67, 29.55, 29.45, 26.17, 22.78, 14.22 ppm. HRMS-E1 (m/z): [M]+ calcd. for C30H56N2O2, 476.43418. found 476.43449.