2-Methylindole → 2-Methyl-5-nitro-1H-indole

HRID 2292764Notes

Reaction equation

HRID 2292764 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[Na+].[CH3:6][C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2>S(=O)(=O)(O)O>[CH3:6][C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([N+:1]([O-:4])=[O:2])=[CH:11][CH:10]=2

Participants

4

Reactant 2

HCID 72242-MethylindoleHCID 24268Sodium Nitrate

Product 1

HCID 2803132-Methyl-5-nitro-1H-indoleYield 59.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of 17.0 g (0.2 mol) of sodium nitrate in 150 mL of sulfuric acid was added dropwise to 26.9 g (0.205 mol) of 2-methyl-1H-indole in 150 mL of sulfuric acid keeping the temperature at -10° to 0° C. with an ethanol-water bath. After 0.25 hours, the mixture was poured onto ice, extracted with EtOAc, the EtOAc solution washed with water, Na2 CO3 solution and dried (Na2SO4). After concentrating at reduced pressure, the residue was crystallized from EtOH to give 20.86 g (59% yield) of 2-methyl-5-nitro-1H-indole, mp, 163°-165° C.

Workup

  1. additionthe mixture was poured onto ice
  2. extractionextracted with EtOAc
  3. washthe EtOAc solution washed with water, Na2 CO3 solution
  4. dry with materialdried (Na2SO4)
  5. concentrationAfter concentrating at reduced pressure
  6. customthe residue was crystallized from EtOH

Sources & evidence

ORD record
ord-86e136b2460b47f694d0eb0de00a0946
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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