Methyl iodide → HCID 67375715, compound

HRID 1678374Notes

Reaction equation

HRID 1678374 reaction equation
C([C:3]1[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=CC=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[C:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15]([CH3:3])([CH3:25])[C:7]=2[CH:6]=[CH:20][CH:21]=1)#[N:19]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 27248729H-fluorene-4-carbonitrile

Product 1

HCID 67375715HCID 67375715, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.25 g of 4-cyanofluorene, 2.6 g of sodium hydride (60% in oil) and 50 ml of NMP are stirred at room temperature for 2 hours. Then, 9.3 g of methyl iodide are added to the reaction mixture drop-wisely and stirred for an additional 2 hours at room temperature. The reaction mixture is poured into 100 ml of water and filtered. The crude product is purified by column chromatography, giving 3.9 g (80%) of 4-cyano-9,9-dimethylfluorene.

Workup

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

Sources & evidence

ORD record
ord-0c94a0a8647b4041860572575cdef0ce
Source dataset
uspto-grants-2011_08
Patent number
US08008507B2

Reaction notes

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