Carbon Dioxide → Methyl 6-amino-2-methyl-3-nitrobenzoate

HRID 343746

Reaktionsgleichung

Reaktionsgleichung von HRID 343746
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([NH2:14])[C:3]=1[C:4]([OH:6])=[O:5].[C:15](=O)([O-])O.[Na+].C(=O)=O.S(OC)(OC)(=O)=O.[Na]>CC(C)=O.O>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([NH2:14])[C:3]=1[C:4]([O:6][CH3:15])=[O:5]

Komponenten

8

Edukt 5

HCID 280Carbon DioxideHCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 152831726-Amino-2-methyl-3-nitrobenzoic acid2×

Produkt 1

HCID 15334532Methyl 6-amino-2-methyl-3-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

49.7 g (0.253 mol) of 2-methyl-3-nitro-6-aminobenzoic acid are dissolved in 380 ml of acetone and 43 g (0.51 mol) of sodium hydrogen carbonate are added. The mixture is then heated to boiling until evolution of CO2 is complete. 35.3 g (0.28 mol) of dimethyl sulfate are then added dropwise in the course of two hours at the boiling point of acetone to the suspension of the sodium salt of 2-methyl-3-nitro-6-aminobenzoic acid thus obtained, and the mixture is subsequently refluxed for a further three hours and then allowed to cool. After pouring the reaction mixture into 1.8 l of water, it is extracted with methylene chloride. After drying, the organic phase is concentrated. The solid obtained is sufficiently pure for the subsequent reaction (NMR). Yield: 50 g (0.238 mol)=94% of theory, m.p.: 92°-94° C.

Aufarbeitung

  1. temperatureThe mixture is then heated
  2. customthus obtained
  3. temperaturethe mixture is subsequently refluxed for a further three hours
  4. temperatureto cool
  5. extractionis extracted with methylene chloride
  6. customAfter drying
  7. concentrationthe organic phase is concentrated
  8. customThe solid obtained
  9. customis sufficiently pure for the subsequent reaction (NMR)

Quellen und Nachweise

ORD-Eintrag
ord-2969ee246e8847f390c9589c6bc88f54
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05863864

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