Ethanol → 2-Amino-9,10-dihydrophenanthrene

HRID 68492Notes

Reaction equation

HRID 68492 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)[CH2:8][CH2:7][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)[CH2:8][CH2:7][C:6]=2[CH:5]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 792362-Nitro-9,10-dihydrophenanthrene

Product 1

HCID 4071852-Amino-9,10-dihydrophenanthreneYield 90.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

First, 280 g of 2-nitro-9,10-dihydrophenanthrene, 2.0 g of palladium carbon, and 2.5 L of ethanol were loaded, and then 140 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 5 L of water. Then, the mixture was extracted with 3 L 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, 220 g of a pale yellow solid were obtained (in 89% yield).

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. extractionThen, the mixture was extracted with 3 L 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-7bdbb7cd37814c12b00e5224112a8462
Source dataset
uspto-grants-2014_09
Patent number
US08822041B2

Reaction notes

Loading…