Methyl iodide → 1-Methyl-7-benzoylindoline

HRID 27360Notes

Reaction equation

HRID 27360 reaction equation
[H-].[Na+].[C:3]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[NH:18][CH2:17][CH2:16]2)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:20]I>CN(C)C=O>[CH3:20][N:18]1[C:19]2[C:15](=[CH:14][CH:13]=[CH:12][C:11]=2[C:3](=[O:10])[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27418922,3-dihydro-1H-indol-7-yl(phenyl)methanone

Product 1

HCID 233426791-Methyl-7-benzoylindoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

To a stirred slurry of 4.8 grams (0.1 mole) of 50% sodium hydride/oil in 100 ml. of dimethylformamide is added dropwise a solution of 22.3 grams (0.1 mole) of 7-benzoylindoline in 50 ml of dimethylformamide. After addition is complete, the mixture is warmed at 50° C. until all solids dissolve. While maintaining the mixture at 50° C., 9.5 grams (0.1 mole) of methyl iodide is added dropwise to the mixture. The mixture is stirred for 4 hours. The mixture is poured into 2 liters of ice water and extracted with 3 portions of 300 ml of benzene. The benzene extracts are combined, washed with water, dried over sodium sulfate and concentrated to give 1-methyl-7-benzoylindoline as a residue.

Workup

  1. additionAfter addition
  2. dissolutiondissolve
  3. temperatureWhile maintaining the mixture at 50° C.
  4. extractionextracted with 3 portions of 300 ml of benzene
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-19dca3fa8ac8437db49bc14dea990e6b
Source dataset
uspto-grants-1980_09
Patent number
US04221716

Reaction notes

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