Methanol → methyl2-(7-amino-4-methyl-2-oxo-2H-chromen-3-yl)acetate

HRID 2369748

Reaktionsgleichung

Reaktionsgleichung von HRID 2369748
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:17])=[C:7]([CH2:13][C:14]([OH:16])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[CH3:18]O>OS(O)(=O)=O>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:17])=[C:7]([CH2:13][C:14]([O:16][CH3:18])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 1293677-Amino-4-methylcoumarin-3-acetic acid

Produkt 1

HCID 86668467methyl2-(7-amino-4-methyl-2-oxo-2H-chromen-3-yl)acetateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidKatalysator

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

7-Amino-4-methyl-3-coumarinylacetic acid (43.1 mg, 0.18 mmol) was dissolved in MeOH (40 ml). H2SO4 (5 drops) was added, and the reaction mixture was heated to 120° C. and stirred. After 4 hr, the disappearance of the starting materials was confirmed, and the reaction mixture was cooled to room temperature. The reaction mixture was concentrated to ⅓ and the mixture was neutralized with aqueous saturated NaHCO3 solution. The reaction mixture was extracted with BuOH, and the organic layer was concentrated. The residue was purified by silica gel column chromatography (eluate: hexane:EtOAc=1:2) to give the object compound (34.4 mg, 0.14 mmol, 75%).

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. extractionThe reaction mixture was extracted with BuOH
  4. concentrationthe organic layer was concentrated
  5. customThe residue was purified by silica gel column chromatography (eluate: hexane:EtOAc=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-3954169c5b93459d91dc616754cf0221
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08709721B2

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