3-Methyl-2-butanone → 2,3,3-Trimethyl-4,6-dicarboxy-3H-indole

HRID 1184955

Reaktionsgleichung

Reaktionsgleichung von HRID 1184955
[NH:1]([C:3]1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[CH:6]=[C:7]([C:9]([OH:11])=[O:10])[CH:8]=1)N.[CH:15]([C:18]([CH3:20])=O)([CH3:17])[CH3:16]>C(O)(=O)C>[CH3:20][C:18]1[C:15]([CH3:17])([CH3:16])[C:4]2[C:3](=[CH:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][C:5]=2[C:12]([OH:14])=[O:13])[N:1]=1

Komponenten

4

Edukt 2

HCID 112513-Methyl-2-butanoneHCID 27723645-Hydrazinylbenzene-1,3-dicarboxylic acid

Produkt 1

HCID 666034172,3,3-Trimethyl-4,6-dicarboxy-3H-indoleAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 5-hydrazinylbenzene-1,3-dicarboxylic acid (30.0 g, 129 mmol), isopropylmethylketone (22.0 mL, 205 mmol) in acetic acid (300 mL) and was heated under reflux in an oil bath for 18 h. After cooling to ambient temperature the solvent was evaporated off under reduced pressure to a small volume of ˜100 mL. To the crude mixture was added iPrOH (200 mL) and the solid was collected with a filter funnel, washed with EtOAc (3×200 mL) and ethyl ether (2×200 mL) and dried. Further drying of the solid in an oven at 50° C. under high vacuum for 18 h provided 30.44 g (95.5%) of the product.

Aufarbeitung

  1. temperatureunder reflux in an oil bath for 18 h
  2. customwas evaporated off under reduced pressure to a small volume of ˜100 mL
  3. additionTo the crude mixture was added iPrOH (200 mL)
  4. customthe solid was collected with a filter funnel
  5. washwashed with EtOAc (3×200 mL) and ethyl ether (2×200 mL)
  6. customdried
  7. customFurther drying of the solid in an oven at 50° C. under high vacuum for 18 h

Quellen und Nachweise

ORD-Eintrag
ord-ae8e963534cc47cb92ba2da591d10979
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669374B2

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