Methanol → Methyl 2-amino-4-methylbenzoate

HRID 574315

Reaktionsgleichung

Reaktionsgleichung von HRID 574315
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:17]O>>[CH3:17][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:7]=1[NH2:6]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 753164-Methylanthranilic acid

Produkt 1

HCID 11205965Methyl 2-amino-4-methylbenzoateAusbeute 82 %

Versuchsvorschrift

Concentrated sulphuric acid (1 mL) was added to a solution of 2-amino-4-methyl-benzoic acid (1.0 g, 6.62 mmol) in dry methanol (10 mL) at 0° C., and then heated at reflux for 16 hr. The mixture was cooled to room temperature and concentrated in vacuo. The crude compound was diluted with water (25 mL) and basified with sodium bicarbonate (10 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL) and the combined organic layers were washed with water (50 mL), brine (50 mL) and dried over sodium sulfate. The organic layer was concentrated under reduced pressure affording 2-amino-4-methyl-benzoic acid methyl ester (900 mg, 82%) as yellow liquid.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 16 hr
  3. concentrationconcentrated in vacuo
  4. additionThe crude compound was diluted with water (25 mL)
  5. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  6. washthe combined organic layers were washed with water (50 mL), brine (50 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationThe organic layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f7a055b4162445569208edc4dad34a54
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034887B2

Verknüpfte Notizen

Wird geladen…