Methanol → Methyl 4-nitroanthranilate

HRID 581661

Reaktionsgleichung

Reaktionsgleichung von HRID 581661
[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:19]O>>[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 120764-Nitroanthranilic acid

Produkt 1

HCID 596476Methyl 4-nitroanthranilateAusbeute 89 %

Versuchsvorschrift

A mixture of 118.8 g of 2-amino-4-nitro-benzoic acid, 1000 ml of methanol and 120 ml of concentrated sulfuric acid is heated at the boiling point for 16 hours. The mixture is concentrated under reduced pressure, the residue is taken up in ethyl acetate and the mixture is washed with saturated NaHCO3 solution. After drying over Na2SO4, the organic phase is concentrated. 114.2 g (89%) of methyl 2-amino-4-nitro-benzoate are thus obtained with a melting point (m.p.) of 156-158° C.

Aufarbeitung

  1. temperatureis heated at the boiling point for 16 hours
  2. concentrationThe mixture is concentrated under reduced pressure
  3. washthe mixture is washed with saturated NaHCO3 solution
  4. dry with materialAfter drying over Na2SO4
  5. concentrationthe organic phase is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-4f8c35cb17de4c0ca3cb4158075d7987
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05922646

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