N~1~,N~1~-Dimethyl-N~3~-(2-nitrophenyl)propane-1,3-diamine → N~1~-[3-(Dimethylamino)propyl]benzene-1,2-diamine
Reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O>[Pd].NN>[CH3:16][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
10.1 g. of o-nitrobromobenzene is reacted, analogously to Example 27, with 5.1 g. of 3-dimethylaminopropylamine, thus obtaining 6 g. of 2-(3-dimethylaminopropylamino)-nitrobenzene, b.p. 138°-141° C. at 0.1 mm Hg. By reducing 3.5 g. of this compound with hydrazine - palladium, 2.9 g. of 2-(3-dimethylaminopropylamino)-aniline is obtained in the form of an oil. 400 mg. of this diamine is reacted with the ethyl ester of 5-nitro-1-methyl-2-imidazolyl-iminocarboxylic acid, as described in Example 1, to obtain 407 mg. of 1-(3-dimethylaminopropyl)-2-(5-nitro-1-methyl-2-imidazolyl)-benzimidazole hydrochloride, m.p. 250° C.
Sources & evidence
- ORD record
- ord-d69eac989db54a64ba84796ac96683d7
- Source dataset
- uspto-grants-1977_10
- Patent number
- US04053472
Reaction notes
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