Hydrazine hydrate (1:1) → N-(2-Dimethylamino-1-methyl-ethyl)-benzene-1,4-diamine
Reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[CH3:5].O.NN>C(O)C.[Ni]>[CH3:16][N:2]([CH3:1])[CH2:3][CH:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1)[CH3:5]Participants
5
Conditions
- Temperature
- 50 °C
Procedure
To a solution of N1,N1-Dimethyl-N2-(4-nitro-phenyl)-propane-1,2-diamine (446 mg, 2 mmol) in absolute ethanol (20 mL) was added hydrazine monohydrate (0.78 mL, 8 equiv.) followed by the addition of a small portion of Raney nickel. The reaction mixture was heated to 50° C. with stirring for 2 h at which point all gas evolution had ceased. The reaction mixture was filtered through celite to remove the Raney nickel. The filtrate was concentrated under reduced pressure to give the N-(2-Dimethylamino-1-methyl-ethyl)-benzene-1,4-diamine as a brown oil. This material was carried on in subsequent steps without purification.
Workup
- filtrationThe reaction mixture was filtered through celite
- customto remove the Raney nickel
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-410221f7e6534ae199c2070f3af32742
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07749530B2
Reaction notes
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