Hydrazine hydrate (1:1) → HCID 20191281, compound

HRID 267752Notes

Reaction equation

HRID 267752 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][C:35]=1[N+:36]([O-])=O)[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[C:23]([N+:30]([O-])=O)[CH:22]=1)([O-])=O.O.NN>[Pd].C(O)C>[NH2:30][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[NH2:27])[O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[O:7][C:6]1[CH:33]=[CH:34][C:35]([NH2:36])=[C:4]([NH2:1])[CH:5]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21554058HCID 21554058, compound

Product 1

HCID 20191281HCID 20191281, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A stirred mixture of 2,2'-bis(3,4-dinitrophenoxy)biphenyl (22.0 g, 0.0425 mole) and 10 weight percent palladium on charcoal (2.2 g) in absolute ethanol (500 ml) was heated to reflux under nitrogen, and a solution of hydrazine hydrate (43 ml) in ethanol (100 ml) was added dropwise over a period of 40 minutes. The reaction mixture was heated at reflux for 17 hours, chilled in an ice bath, and suction filtered through Celite filter aid into one liter of stirred, cold, concentrated hydrochloric acid. The resulting precipitate of hydrazine hydrochloride and desired tetraamine hydrochloride was collected, partially dried and dissolved in water (1 liter). Concentrated ammonium hydroxide solution (300 ml) was added and the resulting precipitate collected and vacuum dried to produce 14.9 g (88 percent) of 2,2'-bis(3,4-diaminophenoxy)biphenyl). A portion of the product was recrystallized from ethanol-water to provide an analytical sample (melting point 172°-174°C).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 17 hours
  5. temperaturechilled in an ice bath
  6. filtrationsuction filtered through Celite
  7. filtrationfilter aid into one liter
  8. customThe resulting precipitate of hydrazine hydrochloride and desired tetraamine hydrochloride was collected
  9. custompartially dried
  10. dissolutiondissolved in water (1 liter)
  11. additionConcentrated ammonium hydroxide solution (300 ml) was added
  12. customthe resulting precipitate collected
  13. customvacuum dried

Sources & evidence

ORD record
ord-3835212d13cc4b92a70639931d186115
Source dataset
uspto-grants-1976_03
Patent number
US03944575

Reaction notes

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