Hydrochloric Acid → 2-(3-Dibutylaminopropylamino)-nitrobenzene

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1Br)([O-:3])=[O:2].[CH2:11]([N:15]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][NH2:19])[CH2:12][CH2:13][CH3:14].C([O-])(=O)C.[Na+].Cl>>[CH2:11]([N:15]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][NH:19][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:12][CH2:13][CH3:14]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 16263-(Dibutylamino)propylamine

HCID 113411-Bromo-2-nitrobenzene

HCID 517045Sodium Acetate

Product 1

HCID 214046762-(3-Dibutylaminopropylamino)-nitrobenzene

Procedure

15 g. of o-nitrobromobenzene and 13 g. of 3-dibutylaminopropylamine are agitated with 15 g. of anhydrous sodium acetate for 7 hours at 135° C. The reaction mixture is taken up in 70 ml. of 6N hydrochloric acid and 80 ml. of water, the unreacted o-nitrobromobenzene is subjected to steam distillation, the distillation residue is rendered alkaline with potassium hydroxide solution, and extracted with ether. After distilling the residue of the ether extract, 12 g. of 2-(3-dibutylaminopropylamino)-nitrobenzene is obtained, b.p. 140°-160° C. at 0.1 mm Hg.