Methyl iodide → 1-Methyl-6-nitro-1H-indole

HRID 1896783Notes

Reaction equation

HRID 1896783 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:13]1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+].CI>O1CCCC1>[CH3:13][N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH:8]=[CH:9]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 2855718-Crown-6HCID 785026-Nitro-1H-indoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 106073591-Methyl-6-nitro-1H-indoleYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-nitro-1H-indole (100 mg, 0.62 mmol) and 18-Crown-6 (180 mg, 0.68 mmol) in anhydrous tetrahydrofuran (2 mL) at room temperature was slowly added potassium tert-butoxide (76 mg, 0.68 mmol) followed by methyl iodide (42 μL, 0.68 mmol). The solution was stirred at room temperature for 30 min. Tetrahydrofuran was removed in vacuo. Ethyl acetate was added, and the organic layer was washed with water and then brine. The combined organic layers were dried over anhydrous MgSO4 and evaporated to afford 91 mg (84%) of the title compound.

Workup

  1. customat room temperature
  2. customTetrahydrofuran was removed in vacuo
  3. additionEthyl acetate was added
  4. washthe organic layer was washed with water
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-b68fa27597c44f5db5a5a597927c45cb
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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