Methyl iodide → Methyl 3-methoxy-4-((1-methyl-5-nitro-1H-indol-3-yl)methyl)benzoate

HRID 1198189Notes

Reaction equation

HRID 1198189 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=2)[NH:18][CH:17]=1)[C:8]([O:10][CH3:11])=[O:9].[CH3:28]I>O1CCCC1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=2)[N:18]([CH3:28])[CH:17]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 114732633-(2-Methoxy-4-methoxycarboxybenzyl)-5-nitroindole

Product 1

HCID 11772604Methyl 3-methoxy-4-((1-methyl-5-nitro-1H-indol-3-yl)methyl)benzoateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (212 milligrams) was added to a solution of methyl 3-methoxy-4-(5-nitroindol-3-ylmethyl)benzoate (1.8 grams) in 60 mL of dry tetrahydrofuran. After stirring for 10 minutes, methyl iodide (753 milligrams) was added and the reaction was stirred at room temperature for 2 hours. The volatiles were evaporated and the residue dissolved in ethyl acetate. The ethyl acetate layer was washed with water, dried over sodium sulfate and evaporated. The residue was purified on silica gel with dichloromethane to give 1.8 grams product, m.p. 151°-153°.

Workup

  1. stirringthe reaction was stirred at room temperature for 2 hours
  2. customThe volatiles were evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified on silica gel with dichloromethane

Sources & evidence

ORD record
ord-cb0d0bd3f6754abd8dde4525b2f18f23
Source dataset
uspto-grants-1994_01
Patent number
US05280039

Reaction notes

Loading…