3-(4-Hydroxyphenyl)-7-methoxy-2-methyl-1(2H)-isoquinolinone → 2-methyl-3-[4-(2,3-epoxypropoxy)-phenyl]-7-methoxy-isoquinolin-1(2H)-one

HRID 262484Notes

Reaction equation

HRID 262484 reaction equation
[K].[CH3:2][C:3](C)([O-:5])[CH3:4].[CH3:7][N:8]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[CH:16][C:15]2[C:10](=[CH:11][C:12]([O:25][CH3:26])=[CH:13][CH:14]=2)[C:9]1=[O:27]>CS(C)=O>[CH3:7][N:8]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:2][CH:3]3[O:5][CH2:4]3)=[CH:20][CH:19]=2)=[CH:16][C:15]2[C:10](=[CH:11][C:12]([O:25][CH3:26])=[CH:13][CH:14]=2)[C:9]1=[O:27]

Participants

4

Reactant 2

HCID 213190573-(4-Hydroxyphenyl)-7-methoxy-2-methyl-1(2H)-isoquinolinoneHCID 50987170Potassium tertbutoxide

Product 1

HCID 213190402-methyl-3-[4-(2,3-epoxypropoxy)-phenyl]-7-methoxy-isoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.35 gm (10 mmols+20%) of potassium-tert.butoxide were added to a solution of 2.8 gm (10 mmols) of 2-methyl-3-(4-hydroxy-phenyl)-7-methoxy-isoquinolin-1(2H)-one in 20 ml of dimethylsulfoxide, while stirring; the potassium salt precipitated out after a short time. 2.8 ml of epibromohydrin were now added, and the mixture was stirred at room temperature until the reaction had gone to completion. The reaction mixture was then poured into ice water, and the cristalline precipitate was collected by suction filtration, washed and dried.

Workup

  1. customthe potassium salt precipitated out after a short time
  2. addition2.8 ml of epibromohydrin were now added
  3. stirringthe mixture was stirred at room temperature until the reaction
  4. additionThe reaction mixture was then poured into ice water
  5. filtrationthe cristalline precipitate was collected by suction filtration
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-d50dd47d9dcf47e4b608870953af9d16
Source dataset
uspto-grants-1979_05
Patent number
US04154837

Reaction notes

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