Acridone → 9-(p-Vinylphenyl)acridine

HRID 259352

Reaction equation

HRID 259352 reaction equation
[Mg].Br[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH2:8])=[CH:5][CH:4]=1.[CH:11]1[C:24]2[C:23](=O)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]=2[CH:14]=[CH:13][CH:12]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O1CCCC1.C1C=CC=CC=1>[CH:7]([C:6]1[CH:9]=[CH:10][C:3]([C:23]2[C:24]3[C:15]([N:16]=[C:17]4[C:22]=2[CH:21]=[CH:20][CH:19]=[CH:18]4)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:5]=1)=[CH2:8]

Participants

7

Reactant 4

HCID 2015AcridoneHCID 14812Phosphorus oxide (P4O10)HCID 162634-BromostyreneHCID 5462224Magnesium2×

Product 1

HCID 227608709-(p-Vinylphenyl)acridineYield 42.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Into a four-neck flask equipped with a stirrer, a nitrogen gas inlet tube, a reflux condenser with a calcium chloride tube and a dropping funnel were charged 4.9 g of magnesium cut powder and 50 ml of tetrahydrofuran. 36.6 Grams of p-bromostyrene diluted with tetrahydrofuran to about 4 times the weight was added dropwise under gentle reflux in a dry nitrogen gas stream. After the magnesium had disappeared, a solution consisting of 37.0 g of acridone and 600 ml of tetrahydrofuran was added dropwise over a period of two hours with stirring. After refluxing for further 5 hours, the reaction mixture was allowed to cool and then poured onto hydrochloric acid-ice to effect hydrolysis. The organic layer was extracted with ether and the extract was dried over anhydrous sodium sulfate. The solvent was then distilled off to obtain a yellow semi-solid. Almost the same weight (60 g) of phosphorus pentoxide was added to 500 ml of a solution of the semi-solid in benzene. The mixture was stirred at room temperature for 5 hours and then allowed to stand overnight. The supernatant liquid separated by decantation was washed with water, dried, and then concentrated to dryness. The residue was purified by silica gel chromatography to obtain 22.5 g of 9-(p-vinylphenyl)acridine. Yield 42.1%.

Workup

  1. customInto a four-neck flask equipped with a stirrer, a nitrogen gas inlet tube, a reflux condenser with a calcium chloride tube and a dropping funnel
  2. additionwas added dropwise
  3. temperatureunder gentle reflux in a dry nitrogen gas stream
  4. additionwas added dropwise over a period of two hours
  5. temperatureAfter refluxing for further 5 hours
  6. temperatureto cool
  7. additionpoured onto hydrochloric acid-ice
  8. customhydrolysis
  9. extractionThe organic layer was extracted with ether
  10. dry with materialthe extract was dried over anhydrous sodium sulfate
  11. distillationThe solvent was then distilled off
  12. customto obtain a yellow semi-solid
  13. stirringThe mixture was stirred at room temperature for 5 hours
  14. customThe supernatant liquid separated by decantation
  15. washwas washed with water
  16. customdried
  17. concentrationconcentrated to dryness
  18. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-82ce3c7a56db4801884c65dfdfdef387
Source dataset
uspto-grants-1977_07
Patent number
US04037036

Linked notes

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