Methyl iodide → HCID 19872252, compound

HRID 477715Notes

Reaction equation

HRID 477715 reaction equation
[CH2:1]([C:5]1([CH2:15][CH:16]([CH3:18])[CH3:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[C:6]1[CH3:14])[CH:2]([CH3:4])[CH3:3].[CH3:19][I:20]>>[I-:20].[CH2:1]([C:5]1([CH2:15][CH:16]([CH3:18])[CH3:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N+:7]([CH3:19])=[C:6]1[CH3:14])[CH:2]([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 19872254HCID 19872254, compound

Product 1

HCID 19872252HCID 19872252, compound

Procedure

3,3-Diisobutyl-2-methyl-(3H)-indole (2.43 g, 0.01 mole) and methyl iodide (3 g, excess) were heated in a flask with condenser on a steam bath for 30 min. The excess methyl iodide was evaporated, and the resulting syrup was dissolved in a small amount of methanol and diluted to 350 mL with ether while stirring in a beaker. After stirring for 20 min., the product was filtered, washed with ether, and dried to give 3.0 g (77.8%). The NMR was good. (MW 385.33)

Workup

  1. customThe excess methyl iodide was evaporated
  2. dissolutionthe resulting syrup was dissolved in a small amount of methanol
  3. additiondiluted to 350 mL with ether
  4. stirringAfter stirring for 20 min.
  5. filtrationthe product was filtered
  6. washwashed with ether
  7. customdried
  8. customto give 3.0 g (77.8%)

Sources & evidence

ORD record
ord-6f66852677d240dfa2eee495bcb0ce6a
Source dataset
uspto-grants-1989_12
Patent number
US04889410

Reaction notes

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