Hydrochloric Acid → 3-(5-Dimethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one

HRID 492166ノート

反応式

HRID 492166 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Li]CCCC.CCCCCC.[CH3:22][N:23]([CH3:34])[C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:29](=O)[O:28][CH2:27]2.Cl.[OH-].[Na+]>COCCOC>[CH3:22][N:23]([CH3:34])[C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:29](=[C:3]1[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]1=[O:10])[O:28][CH2:27]2

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 321710OxindoleHCID 34010695-DimethylaminophthalideHCID 178418244HCID 178418244、化合物

生成物 1

HCID 688381003-(5-Dimethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one収率 60%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
0 °C

実験手順

A solution of oxindole (938 mg, 7.05 mmol) in 20 mL of DME was cooled to 0° C., and treated with 6.2 mL of 2.5M n-BuLi/hexane solution (15.5 mmol) dropwise under nitrogen. The mixture was stirred at 0° C. for 10 minutes. 5-dimethylaminophthalide (1.0 g, 5.64 mmol) was added as one portion. The mixture was allowed to warm to room temperature under nitrogen and stirring was continued for 3 hours. The cloudy mixture was then slowly added into 0.5M aqueous HCl solution (0° C.) with vigorous stirring. The resulting mixture was neutralized with 1M NaOH solution until pH=9. The yellow precipitate which formed was collected by filtration, washed with water, dried under vacuum. The solid obtained was triturated with hot MeOH (20 mL), collected by filtration and dried to give title compound (990 mg, 60%) as a bright yellow powder.

後処理

  1. temperatureto warm to room temperature under nitrogen
  2. stirringstirring
  3. waitwas continued for 3 hours
  4. customThe yellow precipitate which formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried under vacuum
  8. customThe solid obtained
  9. customwas triturated with hot MeOH (20 mL)
  10. filtrationcollected by filtration
  11. customdried

出典と根拠

ORDレコード
ord-82783a6807fa475285566b3f78c6e02d
出典データセット
uspto-grants-2009_05
特許番号
US07531665B2

反応ノート

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