N,N-Dimethylaniline → HCID 22414869, compound

HRID 1721424Notes

Reaction equation

HRID 1721424 reaction equation
C([O:4][C:5]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]2[C:6]=1[C:7]([CH3:17])([CH3:16])[C:8](=[O:15])[NH:9]2)C=C.CN(C)[C:20]1[CH:25]=CC=C[CH:21]=1>>[CH2:25]([C:13]1[C:5]([OH:4])=[C:6]2[C:10](=[C:11]([CH3:14])[CH:12]=1)[NH:9][C:8](=[O:15])[C:7]2([CH3:16])[CH3:17])[CH:20]=[CH2:21]

Participants

3

Reactant 2

HCID 949N,N-Dimethylaniline2×HCID 22414817HCID 22414817, compound

Product 1

HCID 22414869HCID 22414869, compound

Conditions

Temperature
205 °C

Procedure

5.67 g (24.5 mmol) of 4-allyloxy-2,3-dihydro-3,3,7-trimethyl-1H-indol-2-one was added to 13 ml of N,N-dimethylaniline and the mixture was heated with stirring for 17 hours at 205° C. under a nitrogen atmosphere. After the reaction, N,N-dimethylaniline was removed by evaporation under reduced pressure. The residue was dissolved in chloroform and washed with water, 2N hydrochloric acid, and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue obtained was purified by column chromatography (silica gel, 10:1 mixture of chloroform and ethyl acetate) and precipitated in n-hexane. Filtration of the precipitate afforded 4.77 g (yield, 84.1%) of light yellow crystals of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. customwas removed by evaporation under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with water, 2N hydrochloric acid, and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by column chromatography (silica gel, 10:1 mixture of chloroform and ethyl acetate)
  9. customprecipitated in n-hexane
  10. filtrationFiltration of the precipitate
  11. customafforded

Sources & evidence

ORD record
ord-c1f50e3cbdc44ec09c1254996aa28433
Source dataset
uspto-grants-1996_04
Patent number
US05510366

Reaction notes

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