Nitric Acid → 3H-Indole, 2,3,3-trimethyl-5-nitro-

HRID 1516868Notes

Reaction equation

HRID 1516868 reaction equation
[CH3:1][C:2]1[C:10]([CH3:12])([CH3:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[N+:13]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH3:1])[C:10]2([CH3:12])[CH3:11])([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 154273H-Indole, 2,3,3-trimethyl-

Product 1

HCID 975513H-Indole, 2,3,3-trimethyl-5-nitro-Yield 74%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5-nitro-2,3,3-trimethylindole (1) was synthesized according to a modified literature procedure (see, Noland, W. E., et al., J. Org. Chem. 3457-3469, 1965). To a solution of 2,3,3-trimethylindole (10.6 g) in concentrated sulfuric acid cooled to 0° C. using an ice/brine bath was added dropwise fuming nitric acid (5.6 mL). The resultant solution was stirred at 0° C. for 1.5 hours; then poured into crushed ice; filtered; and washed with water. The combined filtrate was neutralized to a pH greater than 7. The product precipitated from the neutralized solution and was collected by filtration, washed with water, and dried to provide the desired product 1 (10.1 g, 74% yield): ESI-MS, calculated [M+H]+ 205.1, found 205.0.

Workup

  1. custom5-nitro-2,3,3-trimethylindole (1) was synthesized
  2. additionthen poured
  3. custominto crushed ice
  4. filtrationfiltered
  5. washand washed with water
  6. customThe product precipitated from the neutralized solution
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-5ae9f523f369458a9f91e6adcb4bed16
Source dataset
uspto-grants-2012_07
Patent number
US08227621B2

Reaction notes

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