Hydrazine → HCID 5095613, compound

HRID 418032Notes

Reaction equation

HRID 418032 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=1)([O-])=O.NN>C(O)C.[Pd]>[NH2:1][C:4]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 149914Triphenylene, 2-nitro-

Product 1

HCID 5095613HCID 5095613, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3.1 g (11.3 mmol) of a mixture of 1 and 2-nitrotriphenylene (synthesized according to J. Chem. Soc., 1955, 4482) in about 100 mL of ethanol, 600 mg (0.57 mmol) of Pd/C (10% on activated carbon), and 2.3 g (45.2 mmol) of hydrazine monhydride were charged in a 250 mL round bottle flask. The reaction mixture was heated up to reflex under nitrogen for 2 hours. The reaction mixture was then filtered and the filtrate was concentrated and passed through a silica gel column using 25% ethyl acetate in hexanes as elute. 1 and 2 aminotriphenyl were separated and confirmed by MS and NMR. This reaction yield was 100%.

Workup

  1. temperatureThe reaction mixture was heated up
  2. filtrationThe reaction mixture was then filtered
  3. concentrationthe filtrate was concentrated
  4. washas elute
  5. custom1 and 2 aminotriphenyl were separated
  6. customThis reaction yield was 100%

Sources & evidence

ORD record
ord-f4c757987ef24ca88440e78b9cfff6e3
Source dataset
uspto-grants-2012_01
Patent number
US08092924B2

Reaction notes

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