Methyl iodide → HCID 67374768, compound

HRID 1678373Notes

Reaction equation

HRID 1678373 reaction equation
C(C1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2C=1)#N.[H-].[Na+].C[N:19]1[C:23](=O)[CH2:22][CH2:21][CH2:20]1.[CH3:25]I>O>[C:23]([C:22]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]([CH3:5])([CH3:25])[C:20]=2[CH:21]=1)#[N:19]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 13387N-methyl-2-pyrrolidoneHCID 173029H-Fluorene-2-carbonitrileHCID 24758Sodium hydride

Product 1

HCID 67374768HCID 67374768, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

14.29 g of 2-cyanofluorene, 8.9 g of sodium hydride (60% in oil) and 150 ml of NMP were stirred at room temperature for 2.5 hours. Then, 31.2 g of methyl iodide was added into the reaction mixture drop-wisely and stirred for an additional 2 hours at room temperature. The reaction mixture was poured into 200 ml of water and filtered. The crude product was purified by column chromatography, giving 8.5 g (60%) of 2-cyano-9,9-dimethylfluorene.

Workup

  1. filtrationfiltered
  2. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-629fd7631ef04c8cb68b6765782f2f4c
Source dataset
uspto-grants-2011_08
Patent number
US08008507B2

Reaction notes

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