Methyl Ethyl Ketone → HCID 67782199, compound

HRID 36556Notes

Reaction equation

HRID 36556 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][C:15]1([CH3:28])[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2.CC(CC)=[O:31]>[Cu]>[C:8]1([N:7]([CH:18]2[CH:19]=[CH:20][C:21]3[C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:15]([CH3:28])([CH3:14])[C:16]=3[C:17]2=[O:31])[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 11487DiphenylamineHCID 783259,9-Dimethylfluorene

Product 1

HCID 67782199HCID 67782199, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

16.9 g of diphenylamine, 50.0 g of 9,9-dimethylfluorene, 10.0 g of potassium carbonate anhydride and 3.0 g of copper powder were added to 70 ml of o-dichlorobenze, followed by stirring for 8 hours at 180°-185° C. After the reaction, the reaction mixture was cooled and subjected to filtration. The filtrate was concentrated under reduced pressure to obtain a solid. An appropriate amount of methylethylketone was added to the solid to obtain a crystal. The crystal was recovered by filtration and purified by silica gel column chromatography (eluent: toluene/hexane) to obtain 28.2 g of 2-(N,N-diphenyl)amino-9,9-dimethylfluorenone (Yield: 79%; melting point: 144.2°-145.1° C.).

Workup

  1. customAfter the reaction
  2. temperaturethe reaction mixture was cooled
  3. filtrationsubjected to filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto obtain a solid
  6. customto obtain a crystal
  7. filtrationThe crystal was recovered by filtration
  8. custompurified by silica gel column chromatography (eluent: toluene/hexane)

Sources & evidence

ORD record
ord-cdb3f78f85104f2eb3bed0b3a1f986c9
Source dataset
uspto-grants-1995_05
Patent number
US05415962

Reaction notes

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