Naphthalimide → HCID 14851943, compound

HRID 1032765Notes

Reaction equation

HRID 1032765 reaction equation
[C:1]1(=[O:15])[C:10]2[C:5]3[C:6](=[CH:11][CH:12]=[CH:13][C:4]=3[C:3](=[O:14])[NH:2]1)[CH:7]=[CH:8][CH:9]=2.CC(C)([O-])C.[K+].S(OCCC#C)([C:25]1[CH:31]=CC(C)=[CH:27][CH:26]=1)(=O)=O>CN(C)C=O>[CH2:27]([N:2]1[C:3](=[O:14])[C:4]2[CH:13]=[CH:12][CH:11]=[C:6]3[C:5]=2[C:10](=[CH:9][CH:8]=[CH:7]3)[C:1]1=[O:15])[CH2:26][C:25]#[CH:31]

Participants

5

Reactant 3

HCID 66491NaphthalimideHCID 2720203-Butynyl p-toluenesulfonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 14851943HCID 14851943, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6 g (0.03 mol) of 1H-benz[de]isoquinoline-1,3(2H)-dione. 4 g (0.0355 mol) of potassium t-butoxide, 9 g (0.04 mol of 4-tosyloxy-1-butyne [ref. G. Eglinton and M. C. Whiting, J. Chem. Soc. 3650 (1950)] and 150 ml of dimethylformamide was heated on the steam bath with stirring for 1.5 hours. The bulk of the solvent was then removed under reduced pressure and the remaining suspension was filtered. The filtrate was diluted with water and the precipitated product was collected by filtration and dissolved in methylene chloride. The solution was dried and passed over a plug of silica gel using methylene chloride for elution. The fractions containing clean product were combined and evaporated. Crystallization from methylene chloride/ethanol gave the title compound as colorless needles with m.p. 191°-193° C.

Workup

  1. customThe bulk of the solvent was then removed under reduced pressure
  2. filtrationthe remaining suspension was filtered
  3. additionThe filtrate was diluted with water
  4. filtrationthe precipitated product was collected by filtration
  5. dissolutiondissolved in methylene chloride
  6. customThe solution was dried
  7. washfor elution
  8. additionThe fractions containing clean product
  9. customevaporated
  10. customCrystallization from methylene chloride/ethanol

Sources & evidence

ORD record
ord-da07e2360af849188917a91448547062
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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