N,N-Dimethylaniline → 5-Allyl-2,3-dihydro-4-hydroxy-3,3-dimethyl-1H-indol-2-one

HRID 1721431Notes

Reaction equation

HRID 1721431 reaction equation
C([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[C:7]([CH3:16])([CH3:15])[C:8](=[O:14])[NH:9]2)C=C.CN(C)[C:19]1[CH:24]=CC=C[CH:20]=1>>[CH2:24]([C:13]1[C:5]([OH:4])=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:14])[C:7]2([CH3:15])[CH3:16])[CH:19]=[CH2:20]

Participants

3

Reactant 2

HCID 949N,N-Dimethylaniline2×HCID 224148734-Allyloxy-2,3-dihydro-3,3-dimethyl-1H-indol-2-one

Product 1

HCID 224148355-Allyl-2,3-dihydro-4-hydroxy-3,3-dimethyl-1H-indol-2-one

Conditions

Temperature
205 °C

Procedure

914 mg (4.21 mmol) of 4-allyloxy-2,3-dihydro-3,3-dimethyl-1H-indol-2-one was added to 4 ml of N,N-dimethylaniline, and the mixture was heated for 30 hours at 205° C. while stirring. After the reaction, N,N-dimethylaniline was evaporated under reduced pressure. The residue was dissolved in chloroform, 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, chloroform:ethyl acetate=20:1), washed with ether-n-hexane, and filtered to obtain 890 mg (yield: 97.4%) of a brown oil of the title compound.

Workup

  1. customwas evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with water, 2N hydrochloric acid, and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by column chromatography (silica gel, chloroform:ethyl acetate=20:1)
  8. washwashed with ether-n-hexane
  9. filtrationfiltered

Sources & evidence

ORD record
ord-8cfa9e4b48b6408b82f9e6f333330107
Source dataset
uspto-grants-1996_04
Patent number
US05510366

Reaction notes

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