Hydrochloric Acid → 5-((4-Methoxybenzyl)oxy)-1-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid

HRID 525852Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 525852
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[C:10](=[O:18])[CH:11]=[C:12]([C:15]([OH:17])=[O:16])O[CH:14]=2)=[CH:5][CH:4]=1.[CH3:21][NH2:22].Cl>>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[C:10](=[O:18])[CH:11]=[C:12]([C:15]([OH:17])=[O:16])[N:22]([CH3:21])[CH:14]=2)=[CH:5][CH:4]=1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 150777735-(4-methoxybenzyloxy)-4-oxo-4H-pyran-2-carboxylic acid

Produkt 1

HCID 708124915-((4-Methoxybenzyl)oxy)-1-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acidAusbeute 79 %

Versuchsvorschrift

A mixture of 5-((4-methoxybenzyl)oxy)-4-oxo-4H-pyran-2-carboxylic acid (1.4627 g, 5.30 mmol) and methanamine (11.0 ml, 22.00 mmol) was stirred at room temperature for 20 h, The reaction was concentrated under reduced pressure, and the residue was dissolved in 15 mL of de-ionized water. The aqueous solution was cooled in an ice bath and treated dropwise with 2N hydrochloric acid (3.0 ml, 6.00 mmol). The resulting yellow solid was filtered, washed with water and acetone, and dried to give 5-((4-methoxybenzyl)oxy)-1-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid (1.21 g, 4.18 mmol, 79% yield). LCMS: (M+H)+: 290.1.

Aufarbeitung

  1. concentrationThe reaction was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in 15 mL of de-ionized water
  3. temperatureThe aqueous solution was cooled in an ice bath
  4. filtrationThe resulting yellow solid was filtered
  5. washwashed with water and acetone
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-648f63be3bb74487b1afb6845afa3114
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340556B2

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