Acetone → HCID 131714215, compound

HRID 462813Notes

Reaction equation

HRID 462813 reaction equation
[OH:1][C:2]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=[O:6])[NH:4][CH:3]=1.C[O-].[Na+].[CH2:16]([CH:18]1O[CH2:19]1)Br.CC(C)=[O:23]>CO.C(Cl)(Cl)Cl>[O:23]1[C:3]2[N:4]1[C:5]([C:7]1[C:12]([C:2]=2[O:1][CH2:16][CH2:18][CH3:19])=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6]

Participants

7

Reactant 4

HCID 180AcetoneHCID 18430EpibromohydrinHCID 2319204-Hydroxyisoquinolin-1(2H)-oneHCID 10942334Sodium Methoxide

Product 1

HCID 131714215HCID 131714215, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

16.1 g of 4 -hydroxyisocarbostyril was suspended in 160 ml of methanol, 21.1 g of 28% sodium methylate was added thereto to dissolve, and then 68.5 g of epibromohydrin was added and stirred for 1 hour at inner temperature of 60° C. The resulting reaction mixture was then concentrated under reduced pressure, and the residue obtained was extracted by adding water and chloroform. The chloroform layer thus obtained was washed with a saturated saline solution, dried over anhydrous sodium sulfate, then concentrated under reduced pressure. 11.8 g of the residue was dissolved in a mixed solvent of chloroform and methanol (19:1), purified over a column packed with 100 g of silica gel to obtain 5.0 g of the main fraction. The fraction was then dissolved in a mixed solvent of methanol and chloroform (1:1), then cooled after addition of acetone to separate a crystal. The crystal was taken out by filtration and then dried in vacuo to obtain 4.0 g of 4-(2,3-epoxy)propoxyisocarbostyril. m.p. 145°-149° C.

Workup

  1. dissolutionto dissolve
  2. customThe resulting reaction mixture
  3. concentrationwas then concentrated under reduced pressure
  4. customthe residue obtained
  5. extractionwas extracted
  6. additionby adding water and chloroform
  7. customThe chloroform layer thus obtained
  8. washwas washed with a saturated saline solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. dissolution11.8 g of the residue was dissolved in a mixed solvent of chloroform and methanol (19:1)
  12. custompurified over a column
  13. customto obtain 5.0 g of the main fraction
  14. temperaturecooled
  15. customto separate a crystal
  16. filtrationThe crystal was taken out by filtration
  17. customdried in vacuo

Sources & evidence

ORD record
ord-725c8346e1614ba296ce9697403e9b57
Source dataset
uspto-grants-1985_05
Patent number
US04517365

Reaction notes

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