2,6-Dimethylaniline → 4-Amino-N-(2,6-dimethylphenyl)phthalimide

HRID 406844

反応式

HRID 406844 の反応式
[N+:1]([C:4]1[CH:14]=[C:8]2[C:9]([O:11][C:12](=[O:13])[C:7]2=[CH:6][CH:5]=1)=O)([O-])=O.[CH3:15][C:16]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:17]=1[NH2:18].[Sn](Cl)Cl.[OH-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[NH2:1][C:4]1[CH:14]=[C:8]2[C:7](=[CH:6][CH:5]=1)[C:12](=[O:13])[N:18]([C:17]1[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:16]=1[CH3:15])[C:9]2=[O:11]

参加物

7

反応物 4

HCID 68962,6-DimethylanilineHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 2309764-Nitrophthalic acid anhydride

生成物 1

HCID 1240314-Amino-N-(2,6-dimethylphenyl)phthalimide収率 67.2%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
100 °C

実験手順

A mixture of 5-nitrophthalic anhydride (1.0 g, 5.2 mmol) and 2,6-dimethylaniline (0.65 mL, 5.3 mmol) in acetic acid (50 mL) was heated at 100° C. overnight (14 h). The reaction mixture was cooled, diluted with ethyl acetate and washed with saturated sodium bicarbonate. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The product was dissolved in ethanol (50 mL), tin (II) chloride (1.4 g, 6.2 mmol) was added and the mixture was heated to reflux for 5 h. The reaction mixture was cooled and made basic by adding aqueous 2 N sodium hydroxide. Ethyl acetate was added and the layers were separated. The organic layer was washed with water and saturated sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator to give 5-amino-2-(2,6-dimethylphenyl)isoindoline-1,3-dione (0.93 g, 67%), which was used without further purification.

後処理

  1. temperatureThe reaction mixture was cooled
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe product was dissolved in ethanol (50 mL)
  7. temperaturethe mixture was heated
  8. temperatureto reflux for 5 h
  9. temperatureThe reaction mixture was cooled
  10. customthe layers were separated
  11. washThe organic layer was washed with water and saturated sodium chloride
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated on a rotary evaporator

出典と根拠

ORDレコード
ord-4d6a49c1ecea43d48702d1ccfcf260e5
出典データセット
uspto-grants-2014_06
特許番号
US08754092B2

関連ノート

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