Methyl iodide → 1H-Indole, 1-methyl-5-nitro-

HRID 1066244Notes

Reaction equation

HRID 1066244 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[H-].[Na+].[CH3:15]I>O1CCCC1>[CH3:15][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 225235-NitroindoleHCID 24758Sodium hydride

Product 1

HCID 1473221H-Indole, 1-methyl-5-nitro-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 5-nitroindole (0.20 g) in tetrahydrofuran (2 ml) was added sodium hydride (0.06 g of 60% dispersion in oil) and evolution of gas noted. After stirring for 30 min methyl iodide (0.086 ml) was added to the dark brown reaction mixture and the reaction mixture heated to 65° C. for 2 hr before cooling to room temperature and partitioning between dichloromethane and water. Organic phase separated, washed with sodium thiosulphate solution, dried (Na2SO4) and concentrated to leave sub-title compound as a yellow solid (0.20 g). 1H NMR (DMSO-d6) δ 8.58 (1H, d), 8.04 (1H, dd), 7.65 (1H, d), 7.61 (1H, d), 6.75 (1H, dd), 3.88 (3H, s).

Workup

  1. additionwas added to the dark brown reaction mixture
  2. temperaturebefore cooling to room temperature
  3. custompartitioning between dichloromethane and water
  4. customOrganic phase separated
  5. washwashed with sodium thiosulphate solution
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8b9479073bca40edaadae06cc04679a2
Source dataset
uspto-grants-2001_06
Patent number
US06242470B1

Reaction notes

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