Sulfuric Acid → Methyl 3-amino-2,4,6-trimethylphenylacetate

HRID 2229903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2229903
[C:1]([CH2:3][C:4]1[C:5]([CH3:13])=[C:6]([C:8]([CH3:12])=[CH:9][C:10]=1[CH3:11])[NH2:7])#N.S(=O)(=O)(O)[OH:15].[C:19](=O)([O-])[O-:20].[Na+].[Na+]>CO.O>[NH2:7][C:6]1[C:5]([CH3:13])=[C:4]([CH2:3][C:1]([O:20][CH3:19])=[O:15])[C:10]([CH3:11])=[CH:9][C:8]=1[CH3:12]

Komponenten

6

Edukt 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 108449753-Cyanomethyl-2,4,6-trimethylaniline

Produkt 1

HCID 10560264Methyl 3-amino-2,4,6-trimethylphenylacetateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 3-cyanomethyl-2,4,6-trimethylaniline (see Example 14, procedure C) (5 g, 28.7 mmol) in methanol (30 mL) was added concentrated sulfuric acid (30 mL) with cooling. The resulting mixture was heated under reflux for 8 h before it was allowed to cool to rt and diluted with water (100 mL). The mixture was stripped off methanol and the residue was basified with sodium carbonate and then extracted with ethyl acetate. The organic layer was worked up and concentrated as usual to give the desired compound as an oil (5.2 g, 88%).

Aufarbeitung

  1. temperaturewith cooling
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 8 h before it
  4. extractionextracted with ethyl acetate
  5. concentrationconcentrated as usual

Quellen und Nachweise

ORD-Eintrag
ord-b47951e02e7e46fc8bafa2f30a51b8a4
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420567B1

Notizen zur Reaktion

Wird geladen…