Hydrazine hydrate (1:1) → HCID 15373719, compound

HRID 1739349Notes

Reaction equation

HRID 1739349 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)=[CH:6][CH:5]=1)([O-])=O.O.NN>[Pd].C(O)C>[NH2:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]2[CH:25]=[CH:26][C:4]([NH2:1])=[CH:5][CH:6]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 153737351,2-Bis(4-nitrophenoxy)benzene

Product 1

HCID 15373719HCID 15373719, compoundYield 88.17%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 3 l round-bottomed flask equipped with a magnetic stirrer bar, reflux condenser and dropping funnel was placed 64.20 g (0.182 mol) of 1,2-bis(4-nitrophenoxy)benzene (SI-319), 700 mL ethanol and 2 g 5% palladium on charcoal. The mixture was brought to boil when 200 mL of hydrazine hydrate was added dropwise during a period of 1.5 hours. The mixture was refluxed for a further 3 hours. The hot mixture was then filtered over a filter agent and left to 10 crystallize. The next day the crystals were separated and the liquid volume reduced to 400 mL, from which an additional crop of crystals was filtered off. The combined crystalline product was recrystallized twice from methanol/water (3:1) to yield 41.2 g of off-white crystals. By reducing the liquid volume a second crop of 5.7 g of crystals was obtained (overall yield 88.17% theoretical). Melting point 135-136° C. Elemental analysis: Calc: C, 73.95%, H, 5.51%, 9.59%; Found: C, 74.10%, H, 5.62%, 9.77%.

Workup

  1. customIn a 3 l round-bottomed flask equipped with a magnetic stirrer bar
  2. temperaturereflux condenser
  3. additionwas added dropwise during a period of 1.5 hours
  4. temperatureThe mixture was refluxed for a further 3 hours
  5. filtrationThe hot mixture was then filtered over a filter agent
  6. waitleft to 10
  7. customcrystallize
  8. customThe next day the crystals were separated
  9. filtrationwas filtered off
  10. customThe combined crystalline product was recrystallized twice from methanol/water (3:1)

Sources & evidence

ORD record
ord-414ef336eb9544be885f6dc2629acb31
Source dataset
uspto-grants-1999_10
Patent number
US05965690

Reaction notes

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