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

HRID 972498Notes

Reaction equation

HRID 972498 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

5

Reactant 4

HCID 313Hydrochloric AcidHCID 16263-(Dibutylamino)propylamineHCID 113411-Bromo-2-nitrobenzeneHCID 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.

Workup

  1. distillationof water, the unreacted o-nitrobromobenzene is subjected to steam distillation
  2. extractionextracted with ether
  3. distillationAfter distilling the residue of the ether
  4. extractionextract

Sources & evidence

ORD record
ord-d03452d48ec74e9c883c834156800ac1
Source dataset
uspto-grants-1977_10
Patent number
US04053472

Reaction notes

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