Nitrogen → 9-Phenanthren-3-ylanthracene

HRID 879923Notes

Reaction equation

HRID 879923 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15]2[CH:16]=[C:17]4[C:26](=[CH:27][CH:28]=2)[C:25](C(O)=O)=[CH:24][C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]4=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.N#N.CO.O>N1C2C(=CC=CC=2)C=CC=1.[Cr]([O-])([O-])=O.[Cu+2]>[CH:27]1[C:26]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=[C:15]([C:13]2[C:12]3[C:7]([CH:6]=[C:5]4[C:14]=2[CH:1]=[CH:2][CH:3]=[CH:4]4)=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:28]=1

Participants

6

Reactant 3

HCID 947NitrogenHCID 22242641Methanol--water (1/1)HCID 596294916-Anthracen-9-ylphenanthrene-9-carboxylic acid

Product 1

HCID 596295009-Phenanthren-3-ylanthracene

Reagents, catalysts & solvents 2

HCID 178505374HCID 178505374, compoundCatalystHCID 7047QuinolineSolvent

Procedure

40 g (94 mmol) of 6-anthracen-9-ylphenanthrene-9-carboxylic acid are suspended in 250 ml of quinoline, the suspension is saturated with N2, 11.8 g (38 mmol) of copper chromite are added, and the mixture is heated at the boil for eight hours. The mixture is subsequently poured into 1 l of MeOH/water, and the black solid is filtered off with suction, washed with MeOH and subjected to Soxhlet extraction with CHCl3. Removal of the solvent leaves a greyish solid, which is recrystallised twice from dioxane. The yield is 30.6 g (92%).

Workup

  1. additionare added
  2. temperaturethe mixture is heated at the boil for eight hours
  3. filtrationthe black solid is filtered off with suction
  4. washwashed with MeOH
  5. extractionsubjected to Soxhlet extraction with CHCl3
  6. customRemoval of the solvent
  7. customleaves a greyish solid, which
  8. customis recrystallised twice from dioxane

Sources & evidence

ORD record
ord-fc400d9c518b466e9f83d4d1a64dc280
Source dataset
uspto-grants-2015_03
Patent number
US08993123B2

Reaction notes

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