Hydrazine → N2-isopropyl-1-methyl-1H-benzimidazole-2,5-diamine

HRID 1391526Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of isopropyl-(1-methyl-5-nitro-1H-benzimidazol-2-yl)-amine (2.15 g, 9.2 mmol) and 10% Pd/C (500 mg) in ethanol (60 ml) was added hydrazine (5 ml) and the reaction was heated to 80° C. After TLC showed the starting material to be consumed, the reaction was cooled to rt and passed through a plug of celite. The filtrate was concentrated to give the title compound as an off-white solid. 1H NMR (300 MHz, d6-DMSO) δ 6.75 (d, J=8.1 Hz, 1H), 6.45 (d, J=1.8 Hz, 1H), 6.20 (dd, J=8.1 and 2.1 Hz, 1H), 6.06 (d, J=7.8 Hz, 1H), 4.43 (br s, 2H), 3.96 (m, 1H), 3.35 (s, 3H), 1.19 (d, J=6.6 Hz, 6H).

Workup

customto be consumed
temperaturethe reaction was cooled to rt
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-72ae8455e79e4927b0bc97b50449cd61
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07338959B2

Reaction notes

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