Ethyl Acetate → HCID 13827276, compound

HRID 978656Notes

Reaction equation

HRID 978656 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[NH:15][N:14]=[CH:13]3)=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:23](I)[CH2:24][CH2:25][CH3:26].C(OCC)(=O)C>CS(C)=O>[CH2:23]([N:15]1[N:14]=[CH:13][C:12]2[C:17](=[CH:18][CH:19]=[C:10](/[CH:9]=[CH:8]/[C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)[CH:11]=2)[C:16]1=[O:20])[CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10962Butyl iodideHCID 14798Sodium HydroxideHCID 13827271HCID 13827271, compound

Product 1

HCID 13827276HCID 13827276, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 27.5 gm of trans-6-[2-(4-hydroxyphenyl)ethenyl]-1-(2H)-phthalazinone (as prepared in Example 2) in 1300 ml DMSO was treated with 135 ml 2.5N sodium hydroxide solution, followed by 12.5 ml n-butyl iodide. The reaction mixture was stirred for 21/2 hours, then added to 8000 ml ethyl acetate. After stirring for a few minutes the insoluble material was filtered off and washed with a little ethyl acetate. The ethyl acetate was removed on a rotary evaporator and the residue added to 8000 ml water, stirred for an hour and allowed to settle overnight. The clear supernatant liquid was syphoned off and the residual slurry was filtered and the crude product washed thoroughly with water. After air drying it weighed 24.8 gm. The crude product was recrystallized from 125 ml 2-methoxyethanol, filtered and washed with isopropanol and ether. After drying at 60° for 24 hours, it weighed 17.4 gm and melted at 225°-230° C.

Workup

  1. stirringAfter stirring for a few minutes the insoluble material
  2. filtrationwas filtered off
  3. washwashed with a little ethyl acetate
  4. customThe ethyl acetate was removed on a rotary evaporator
  5. additionthe residue added to 8000 ml water
  6. stirringstirred for an hour
  7. waitto settle overnight
  8. filtrationthe residual slurry was filtered
  9. washthe crude product washed thoroughly with water
  10. customAfter air drying it
  11. customThe crude product was recrystallized from 125 ml 2-methoxyethanol
  12. filtrationfiltered
  13. washwashed with isopropanol and ether
  14. customAfter drying at 60° for 24 hours

Sources & evidence

ORD record
ord-8417e526806c4417b7af0aaccdfc8ee0
Source dataset
uspto-grants-1987_05
Patent number
US04665181

Reaction notes

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