Hydrochloric Acid → Methyl 3-methylanthranilate

HRID 255856

Reaktionsgleichung

Reaktionsgleichung von HRID 255856
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[C:13](=O)(O)[O-].[Na+]>CO>[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]

Komponenten

5

Edukt 3

HCID 313Hydrochloric Acid2×HCID 781012-Amino-3-methylbenzoic acidHCID 516892Sodium Bicarbonate

Produkt 1

HCID 2763406Methyl 3-methylanthranilate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A solution of 60.8 g of 2-amino-3-methylbenzoic acid in 900 ml of dry methanol was saturated with anhydrous hydrogen chloride at 0°-10° C., then allowed to stand at room temperature overnight. Then it was refluxed for one hour, cooled to 5° C., resaturated with anhydrous hydrogen chloride, held overnight at room temperature and stripped of solvent. The residue was made neutral with saturated aqueous sodium bicarbonate solution, and extracted with methylene chloride. The extract phase was washed with saturated aqueous sodium bicarbonate solution, dried (MgSO4), filtered and stripped of solvent. The residue was distilled in a kugelrohr apparatus to give methyl 2-amino-3-methylbenzoate (49A), b.p.: 100°-105° C. (1Torr.).

Aufarbeitung

  1. temperatureThen it was refluxed for one hour
  2. waitheld overnight at room temperature
  3. extractionextracted with methylene chloride
  4. washThe extract phase was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. distillationThe residue was distilled in a kugelrohr apparatus

Quellen und Nachweise

ORD-Eintrag
ord-5076a2f0ee6f4c48b80060ff58c82f44
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04699651

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