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

HRID 1721431ノート

反応式

HRID 1721431 の反応式
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]

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
205 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8cfa9e4b48b6408b82f9e6f333330107
出典データセット
uspto-grants-1996_04
特許番号
US05510366

反応ノート

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