Formaldehyde → 1-Morpholin-4-ylmethyl-3-(1H-pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one

HRID 352293Notes

Reaction equation

HRID 352293 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[C:7]1\[C:8](=[O:16])[NH:9][C:10]2[C:15]\1=[CH:14][CH:13]=[CH:12][CH:11]=2.[CH2:17]=O.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>O1CCOCC1.CCO>[N:19]1([CH2:17][N:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7](=[CH:6][C:2]3[NH:1][CH:5]=[CH:4][CH:3]=3)[C:8]2=[O:16])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 712Formaldehyde2×HCID 8083Morpholine2×HCID 5908088(Z)-3-((1H-pyrrol-2-yl)methylene)indolin-2-one

Product 1

HCID 688658871-Morpholin-4-ylmethyl-3-(1H-pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-oneYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A mixture of Z-(1H-Pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one (120 mg, 0.57 mmol), paraformaldehyde (32 mg, 1.1 mmol), and morpholine (62.2 μL, 0.71 mmol) in 8.0 mL of 20% dioxane in EtOH was heated at reflux for 19.5 h. The reaction mixture was concentrated and paraformaldehyde (10.0 mg, 0.33 mmol), morpholine (15 μL, 0.17 mmol) and EtOH (7 mL) was added. The reaction mixture refluxed for 24 h. The reaction mixture was cooled to room temperature and concentrated. The residue was dissolved in 15 mL of CHCl3 and treated with activated charcoal. The resulting suspension was filtered and the filtrate concentrated. The residue was crystallization from ethyl acetate/hexane to give the title compound (88.0 mg, 50%) as a bright yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 19.5 h
  3. concentrationThe reaction mixture was concentrated
  4. temperatureThe reaction mixture refluxed for 24 h
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in 15 mL of CHCl3
  7. additiontreated with activated charcoal
  8. filtrationThe resulting suspension was filtered
  9. concentrationthe filtrate concentrated
  10. customcrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-eef5c35af7d5402d80d3d18cd6ca9655
Source dataset
uspto-grants-2004_06
Patent number
US06747025B1

Reaction notes

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