Reaktion #1687153

Reaktionsgleichung

2-methyl-3-nitro-6-aminobenzoic acid

sodium hydrogen carbonate

dimethyl sulfate

sodium

2-methyl-3-nitro-6-aminobenzoic acid

CO2

→

Methyl 2-methyl-3-nitro-6-aminobenzoate

Lösungsmittel

water

acetone

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONare added
2. 2
   TemperaturThe mixture is then heated
3. 3
   Sonstigethus obtained
4. 4
   Temperaturandthe mixture is subsequently refluxed for a further 3 hours
5. 5
   Extraktionis extracted with methylene chloride
6. 6
   SonstigeAfter drying
7. 7
   Einengenthe organic phase is concentrated
8. 8
   SonstigeThe solid obtained
9. 9
   Sonstigeis sufficiently pure for the subsequent reaction (NMR)

Vorschrift

49.7 g (0.253 mol) of 2-methyl-3-nitro-6-aminobenzoic acid are dissolved in380 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 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, andthe mixture is subsequently refluxed for a further 3 hours and then allowedto 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.

Quelle