Hydrazine hydrate (1:1) → HCID 20191282, compound

HRID 267753Notes

Reaction equation

HRID 267753 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:31]=[CH:32][C:33]=1[N+:34]([O-])=O)[O:7][C:8]1[C:17]2[C:12](=[C:13]([O:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[C:21]([N+:28]([O-])=O)[CH:20]=3)[CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)([O-])=O.O.NN>[Pd].C(O)C>[NH2:28][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[NH2:25])[O:18][C:13]1[C:12]2[C:17](=[C:8]([O:7][C:6]3[CH:31]=[CH:32][C:33]([NH2:34])=[C:4]([NH2:1])[CH:5]=3)[CH:9]=[CH:10][CH:11]=2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21554060HCID 21554060, compound

Product 1

HCID 20191282HCID 20191282, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A stirred mixture of 1,5-bis(3,4-dinitrophenoxy)naphthalene (6 g, 0.0122 mole) and 10 percent palladium on charcoal (0.6 g) in absolute ethanol (300 ml) was heated to reflux under nitrogen. A solution of hydrazine hydrate (8 ml) in ethanol (30 ml) was added dropwise over a period of 40 minutes. The reaction mixture was heated at reflux for 6 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 the desired tetraamino hydrochloride was collected, partially dried, and dissolved in water (300 ml). Concentrated ammonium hydroxide solution (60 ml) was added and the resulting precipitate collected and vacuum dried to produce 4.5 g (90 percent) of the desired 1,5-bis(3,4-diaminophenoxy)naphthalene. Recrystallization from benzene gave a white product (melting point 230°-231°C).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 6 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 the desired tetraamino hydrochloride was collected
  9. custompartially dried
  10. dissolutiondissolved in water (300 ml)
  11. additionConcentrated ammonium hydroxide solution (60 ml) was added
  12. customthe resulting precipitate collected
  13. customvacuum dried

Sources & evidence

ORD record
ord-b74f56b07f6d47afa08bc6c17835ce39
Source dataset
uspto-grants-1976_03
Patent number
US03944575

Reaction notes

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