Indole → HCID 15389762, compound

HRID 363327Notes

Reaction equation

HRID 363327 reaction equation
[OH-].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[CH:12]1[C:20]2[N:15]([CH:16]=[CH:17][C:18](=O)[CH:19]=2)[CH2:14][CH:13]=1>O>[CH2:12]1[CH:20]2[N:15]([CH2:16][CH:17]=[C:18]([C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:3][CH:4]=3)[CH2:19]2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 798IndoleHCID 14797Potassium HydroxideHCID 69592000HCID 69592000, compound

Product 1

HCID 15389762HCID 15389762, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium hydroxide (10% in methanol, 15 ml, 26.8 mmol), 1H-indole (1.5 g, 13 mmol), and 7-indolizinone (1.39 g, 10 mmol) were combined and heated to reflux for 15 hours. The mixture was diluted with water and the precipitate was filtered. The brown filter cake was triturated with hot methanol, cooled to room temperature, and the solid collected to give 1.99 g of desired product. (84%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 hours
  3. filtrationthe precipitate was filtered
  4. customThe brown filter cake was triturated with hot methanol
  5. customthe solid collected

Sources & evidence

ORD record
ord-268d4a5e8c874b95b629f36694152c89
Source dataset
uspto-grants-1999_02
Patent number
US05874427

Reaction notes

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