Pyrrolidine → 3-Azulen-1-ylmethylene-1,3-dihydro-indol-2-one

HRID 2236122Notes

Reaction equation

HRID 2236122 reaction equation
[CH:1]([C:3]1[C:12]2[C:6]([CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH:5][CH:4]=1)=O.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][C:14]1=[O:22].N1CCCC1>C(O)C>[C:3]1([CH:1]=[C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:13][C:14]2=[O:22])[C:12]2[C:6]([CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 321710OxindoleHCID 117448701-Azulene carboxyaldehyde

Product 1

HCID 573900793-Azulen-1-ylmethylene-1,3-dihydro-indol-2-oneYield 101.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

1-Formylazulene (2 mmol) was dissolved in 40 mL ethanol. 266 mg oxindole (2 mmol) and 200 mL ethanol were then added. Next, a 4 mL solution containing 1M pyrrolidine and ethanol was added to react at room temperature for three days. After removal of solvent, the resulting solution was extracted by 150 mL acetyl acetate and 50 mL water. The resulting solution was extracted again by 50 mL citric acid aqueous solution and ethyl acetate. The ethyl acetate layer was collected, dried with anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was then purified by column chromatography (Silica Gel 60, dichloromethane) and dried to give Compound 001 (552 mg, 95%).

Workup

  1. additionwas added
  2. customto react at room temperature for three days
  3. customAfter removal of solvent
  4. extractionthe resulting solution was extracted by 150 mL acetyl acetate and 50 mL water
  5. extractionThe resulting solution was extracted again by 50 mL citric acid aqueous solution and ethyl acetate
  6. customThe ethyl acetate layer was collected
  7. dry with materialdried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue was then purified by column chromatography (Silica Gel 60, dichloromethane)
  11. customdried

Sources & evidence

ORD record
ord-8733d81c6b964c069b06514496003d58
Source dataset
uspto-grants-2010_05
Patent number
US07714146B2

Reaction notes

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