Formaldehyde → 1-Butylaminomethyl-3-(1H-pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one

HRID 492157Notes

Reaction equation

HRID 492157 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.C=O.[CH2:19]([NH2:23])[CH2:20][CH2:21][CH3:22].[CH3:24]CCCCC>CCO>[CH2:19]([NH:23][CH2:24][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7](=[CH:6][C:2]2[NH:1][CH:5]=[CH:4][CH:3]=2)[C:8]1=[O:16])[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8007ButylamineHCID 8058HexaneHCID 5908088(Z)-3-((1H-pyrrol-2-yl)methylene)indolin-2-one

Product 1

HCID 688346411-Butylaminomethyl-3-(1H-pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of Z-(1H-Pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one (120.0 mg, 0.571 mmol), paraformaldehyde (17.1 mg, 0.571 mmol), and butylamine (56.4 μL, 0.571 mmol) in 5.5 mL of EtOH was heated at reflux for 2.5 h. Then reaction mixture was treated with 2 mL of hexane was and then cooled to 0° C. The reaction mixture was then filtered to remove Z-(1H-Pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one. The filtrate was partitioned between dilute HCl and ethyl acetate. The organic layer was removed and the aqueous layer washed with 15 mL Ethyl acetate. The aqueous phase was made basic to pH 8 with saturated NaHCO3 and extracted with ethyl acetate. The ethyl acetate layer was washed with H2O, brine and dried over anhydrous Na2SO4. The solvent was removed in vacuo to give 58 mg of yellow oil. The oil was purified by chromatography (silica gel, 1:1/hexane:ethyl acetate) to give the title compound (51.6 mg, 31%) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 h
  3. customThen reaction mixture
  4. filtrationThe reaction mixture was then filtered
  5. customto remove Z-(1H-Pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one
  6. customThe filtrate was partitioned between dilute HCl and ethyl acetate
  7. customThe organic layer was removed
  8. washthe aqueous layer washed with 15 mL Ethyl acetate
  9. extractionextracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with H2O, brine
  11. dry with materialdried over anhydrous Na2SO4
  12. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-caaa98972a5a4ee6ade3347f0d69f539
Source dataset
uspto-grants-2009_05
Patent number
US07531665B2

Reaction notes

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