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

HRID 2236123Notes

Reaction equation

HRID 2236123 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.[CH2:13]([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][C:21]1=[O:29])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1CCCC1>C(O)C>[C:3]1([CH:1]=[C:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:20]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:21]2=[O:29])[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 117448701-Azulene carboxyaldehydeHCID 117908211-benzyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 685830393-Azulen-1-ylmethylene-1-benzyl-1,3-dihydro-indol-2-oneYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
40 °C

Procedure

1-Formylazulene (1 mmol) was dissolved in 20 mL ethanol. 223 mg 1-benzylindolin-2-one (1 mmol) and 20 mL ethanol were then added. Next, a 2 mL solution (1 mmol) 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 ethyl 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. Next, methanol was added and ultrasonically shaken at 40° C. for 1 hour. After filtration, washing by methanol, and drying, Compound 002 (315 mg, 87%) was obtained.

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 ethyl 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. additionNext, methanol was added
  11. filtrationAfter filtration
  12. washwashing by methanol
  13. customdrying

Sources & evidence

ORD record
ord-e4cbc6c77b6247c0b34c10def7e47f39
Source dataset
uspto-grants-2010_05
Patent number
US07714146B2

Reaction notes

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