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

HRID 1515209

Reaktionsgleichung

Reaktionsgleichung von HRID 1515209
[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]

Komponenten

7

Edukt 4

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

Produkt 1

HCID 1240314-Amino-N-(2,6-dimethylphenyl)phthalimideAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7f8b0fa4c2d0475ca82d61201a266e59
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222263B2

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