Ethanol → 2-Phenanthrenamine

HRID 68530Notes

Reaction equation

HRID 68530 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7][C:6]=2[CH:5]=1)([O-])=O.C(O)C.O.NN>[C].[Pd].O>[NH2:1][C:4]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7][C:6]=2[CH:5]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 282062-Nitrophenanthrene

Product 1

HCID 768932-PhenanthrenamineYield 86.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

First, 13.4 g of 2-nitrophenanthrene, 0.10 g of palladium carbon, and 120 mL of ethanol were loaded, and then 7 mL of hydrazine monohydrate were added to the mixture. The reaction solution was stirred for 4 hours under heating reflux. After having been cooled to room temperature, the reaction solution was poured into 300 mL of water. Then, the mixture was extracted with 200 mL of toluene. After the water layer had been removed, the organic layer was dried with magnesium sulfate. After magnesium sulfate had been separated by filtration, the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 10.0 g of a pale yellow solid were obtained (in 86% yield).

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. extractionThen, the mixture was extracted with 200 mL of toluene
  4. customAfter the water layer had been removed
  5. dry with materialthe organic layer was dried with magnesium sulfate
  6. customAfter magnesium sulfate had been separated by filtration
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6fca4ab2fe8e4af183a37cd939d24cd2
Source dataset
uspto-grants-2014_09
Patent number
US08822041B2

Reaction notes

Loading…