Potassium Hydroxide → 5-Nitro-3-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1H-indole

HRID 2043517Notes

Reaction equation

HRID 2043517 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].[OH-].[K+].[CH2:15]1[O:25][C:18]2([CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]2)[O:17][CH2:16]1>CO>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:21]1[CH2:22][CH2:23][C:18]2([O:25][CH2:15][CH2:16][O:17]2)[CH2:19][CH:20]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 225235-NitroindoleHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 573848065-Nitro-3-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1H-indoleYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-nitroindole (38) (3.0 g, 18.501 mmol) in dry methanol (50 mL) was treated with KOH (5.6 g) at room temperature. After stifling for 10 min., 1,4-cyclohexanedione monoethylene ketal (7.22 g, 46.253 mmol) was added and the resulting solution was refluxed for 36 h. The reaction was brought to room temperature and solvent was evaporated. Crude was diluted with water (50 mL), precipitated solid was filtered off and washed with water (2×10 mL). The precipitate was dried under vacuum to obtain compound 78 (4.7 g, 85%) as a solid. For spectral data, please see Example 23.

Workup

  1. temperaturethe resulting solution was refluxed for 36 h
  2. customwas brought to room temperature
  3. customsolvent was evaporated
  4. additionCrude was diluted with water (50 mL)
  5. customprecipitated solid
  6. filtrationwas filtered off
  7. washwashed with water (2×10 mL)
  8. customThe precipitate was dried under vacuum

Sources & evidence

ORD record
ord-58c14ef4051b441fb9f2272355d48edd
Source dataset
uspto-grants-2013_11
Patent number
US08586620B2

Reaction notes

Loading…