Methyl iodide → HCID 13133038, compound

HRID 444204Notes

Reaction equation

HRID 444204 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:12]2[NH:13][C:14](=[O:21])[C:15]3[C:20]([C:11]=2[C:10]2[CH:9]=[C:8]([Cl:22])[CH:7]=[CH:6][C:5]1=2)=[CH:19][CH:18]=[CH:17][CH:16]=3.[CH3:23]I>CN(C)C=O>[CH3:23][O:21][C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]2[C:10]3[CH:9]=[C:8]([Cl:22])[CH:7]=[CH:6][C:5]=3[N:4]([CH3:3])[C:12]=2[N:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13133047HCID 13133047, compound

Product 1

HCID 13133038HCID 13133038, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of 0.08 g of 65% sodium hydride (in oil) in 5 ml of dimethylformamide, 0.5 g of 7-methyl-10-chloroindolo(2,3-c)isoquinolin-5(6H)-one is added at room temperature. The reaction mixture is stirred for 30 minutes and 2.5 g of methyl iodide in 30 ml of dimethylformamide is added dropwise thereto at room temperature. After addition, stirring is continued for further 16 hours at room temperature and then dimethylformamide is removed under reduced pressure. The residue is treated with water and extracted with dichloromethane. The organic layer is dried over magnesium sulfate and the solvent is evaporated in vacuo to give 404 mg of 5-methoxy-7-methyl-10-chloro-7H-indolo(2,3-c)isoquinoline, which is recrystallized from ethyl acetate, melting point 179°-180.5° C.

Workup

  1. additionis added at room temperature
  2. customat room temperature
  3. additionAfter addition
  4. stirringstirring
  5. waitis continued for further 16 hours at room temperature
  6. customdimethylformamide is removed under reduced pressure
  7. additionThe residue is treated with water
  8. extractionextracted with dichloromethane
  9. dry with materialThe organic layer is dried over magnesium sulfate
  10. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-6060058f6145427bb2a4acc61ea56e76
Source dataset
uspto-grants-1981_04
Patent number
US04263304

Reaction notes

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