Methyl iodide → HCID 86748552, compound

HRID 1608777Notes

Reaction equation

HRID 1608777 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[C:5](/[CH:12]=[C:13]2\[C:14](=[O:22])[NH:15][C:16]3[C:21]\2=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:4]1.[H][H].I[CH3:26]>CN(C=O)C>[CH3:26][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[C:5](/[CH:12]=[C:13]2\[C:14](=[O:22])[NH:15][C:16]3[C:21]\2=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:4]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10199113HCID 10199113, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86748552HCID 86748552, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 95% sodium hydride (0.280 g, 0.011 mol) in DMF (100 ml) cooled with an ice-n-propanol bath is added over 15 min with stirring a solution of (Z)-3-[(7-azaindol-3-yl)methylen]-2-oxindole (2.61 g, 0.010 mol) in DMF (50 ml). When the evolution of hydrogen stopped, a solution of iodomethane (1.56 g, 0.011 mol) in DMF (50 ml) is added over 15 min and the mixture is stirred at r.t. for 3 h. Most of the DMF is distilled off in vacuo, water is then added to the residue and the product extracted into ethyl acetate. The organic solution containing the desired product is dried (Na2SO4), the solvent evaporated and the remaining oil is crystallized by trituration with ethanol. Thus pure title compound is obtained in 60% yield. C17H13N3O requires : C 74.19 H 4.73 N 15.27 found : C 74.05 H 4.55 N 15.05 MS m/z : 275.

Workup

  1. temperaturecooled with an ice-n-propanol bath
  2. additionis added over 15 min
  3. distillationMost of the DMF is distilled off in vacuo, water
  4. additionis then added to the residue
  5. extractionthe product extracted into ethyl acetate
  6. additionThe organic solution containing the desired product
  7. dry with materialis dried (Na2SO4)
  8. customthe solvent evaporated
  9. customthe remaining oil is crystallized by trituration with ethanol

Sources & evidence

ORD record
ord-8f319331244a42abbb1d65d926fdf35d
Source dataset
uspto-grants-1995_03
Patent number
US05397787

Reaction notes

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