HCID 59129205, compound → 5-Methyl-6-nitro-1H-indole

HRID 386657Notes

Reaction equation

HRID 386657 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[NH:7][CH2:6][CH2:5]2>O1CCOCC1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[NH:7][CH:6]=[CH:5]2

Participants

3

Reactant 1

HCID 59129205HCID 59129205, compound

Product 1

HCID 212183045-Methyl-6-nitro-1H-indoleYield 67.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

5-Methyl-6-nitroindoline (0.75 gr) was dissolved in 20 mL dioxane and treated with 1.5 g of dichloro dicyano quinone. The solution was heated at 80° C. for two hours, then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography to give 0.5 g of 5-methyl-6-nitroindole (e/z (M+H) 177).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e43a2c6cdfb3456ba75f1f582c0d2e14
Source dataset
uspto-grants-2013_02
Patent number
US08372865B2

Reaction notes

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