Acetic Acid → (4-Nitrophenyl)hydrazine

HRID 1196809Notes

Reaction equation

HRID 1196809 reaction equation
BrNC(=O)[CH2:4][CH2:5][C:6]([NH2:8])=O.[NH:10]=[N:11][CH:12]=NN.[CH2:15](O)[CH2:16]CC.C(O)(=[O:22])C.CO.[OH2:26]>C(OCC)(=O)C.O>[N+:8]([C:6]1[CH:16]=[CH:15][C:12]([NH:11][NH2:10])=[CH:4][CH:5]=1)([O-:22])=[O:26]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 2631-ButanolHCID 9834204N-BromosuccinamideHCID 22242641Methanol--water (1/1)HCID 53427792HCID 53427792, compound

Product 1

HCID 3310889(4-Nitrophenyl)hydrazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Next 300 mg of N-bromosuccinamide was added to 1.5 g of the formazan derivative in 200 ml ethyl acetate. After reaction for 0.5 hour under reflux conditions, the product tetrazolium salt was recovered by precipitation with ether as a yellow powder. It was purified by recrystallization from acetone-methanol after charcoal treatment of the hot solution, by pouring the hot filtrate solution into ether. The crystals were collected and dried in vacuum yielding 0.6 g. Based upon the expected formula of C19H11BrIN7O6, the expected elemental analysis is 35.65% C, 1.73% H, 15.32% N and 15% O. Observed were 35.9%, 2.03%, 12.42% and 16.67%, respectively. The product showed a melting point over the 210-217 degree centigrade range, indicating greater than 98% purity. Thin layer chromatography (n-butanol:acetic acid:water at a 78:5:17 volume ratio) showed a single spot with a retention factor of 0.73. U.V. analysis in methanol:water (1:1 by volume) showed a maximum lambda at 240.5 nm and a molar extinction coefficient of 28,600.

Workup

  1. customAfter reaction for 0.5 hour under reflux conditions
  2. customthe product tetrazolium salt was recovered by precipitation with ether as a yellow powder
  3. customIt was purified by recrystallization from acetone-methanol after charcoal treatment of the hot solution
  4. additionby pouring the hot filtrate solution into ether
  5. customThe crystals were collected
  6. customdried in vacuum
  7. customyielding 0.6 g
  8. customover the 210-217 degree centigrade range

Sources & evidence

ORD record
ord-36ea29092424490286266f9eb980aff0
Source dataset
uspto-grants-1992_05
Patent number
US05116732

Reaction notes

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