Water → 5,5-dimethyl-5H-indeno[1,2-b]pyridine

HRID 1775395Notes

Reaction equation

HRID 1775395 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2CC3[C:13]([C:2]=12)=[CH:12][CH:11]=[CH:10][CH:9]=3.[CH3:14][C:15]([CH3:18])([O-])[CH3:16].[K+].IC.O>O1CCCC1>[CH3:14][C:15]1([CH3:18])[C:3]2[C:2](=[N:1][CH:6]=[CH:5][CH:4]=2)[C:13]2[C:16]1=[CH:9][CH:10]=[CH:11][CH:12]=2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 92054-AzafluoreneHCID 23665647Potassium tert-butoxide

Product 1

HCID 578727185,5-dimethyl-5H-indeno[1,2-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

13.5 g (80.7 mmol) of 5H-indeno[1,2-b]pyridine was dissolved in 120 ml dry tetrahydrofuran, and 22.7 g (202 mmol) of potassium tert-butoxide was added to the solution at −10° C. The reaction mixture was maintained at −10° C. for 1 hour. Then the iodomethane 28.7 g (202 mmol) was added dropwise; the solution was then warmed slowly to room temperature and stirred for 6 h. After the reaction completion, water was added to the mixture to terminate the reaction. The reaction mixture was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was evaporated in vacuo, and the residue was crystallized with toluene to give the 5,5-dimethyl-5H-indeno[1,2-b]pyridine, 13.5 g (86%)

Workup

  1. temperaturethe solution was then warmed slowly to room temperature
  2. customto terminate
  3. customthe reaction
  4. extractionThe reaction mixture was extracted with ethyl acetate and water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customthe residue was crystallized with toluene

Sources & evidence

ORD record
ord-b889ee7e909f460ead1e4d3a19d35bbc
Source dataset
uspto-grants-2016_02
Patent number
US09260363B2

Reaction notes

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