Hydrochloric Acid → 2-Oxo-1-phenyl-1,2-dihydropyridine-3-carboxylic acid

HRID 1670276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1670276
[O:1]=[C:2]1[C:7]([C:8]([O:10]C)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Li+].[OH-].CCOC(C)=O.Cl>CO.O>[O:1]=[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 59852857Methyl 2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylate

Produkt 1

HCID 210815852-Oxo-1-phenyl-1,2-dihydropyridine-3-carboxylic acidAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylate (70 mg, 0.31 mmol) and LiOH (40 mg) in methanol (6 mL) and water (1 mL) was stirred at rt overnight. To the reaction mixture were added EtOAc (50 mL) and 1 N aq HCl (15 mL). The EtOAc layer was separated, dried over MgSO4, and concentrated in vacuo to afford the product (55 mg, 83%) as a light yellow solid. 1H NMR (DMF-d7) δ 11.77 (br s, 1H), 8.57 (dd, 1H, J=7.4, 2.0 Hz), 8.26 (dd, 1H, J=6.6, 1.6 Hz), 7.64-7.55 (m, 5H), 6.88 (t, 1H, J=7.0 Hz); MS (ESI+) m/z 216.2 (M+H)+.

Aufarbeitung

  1. customThe EtOAc layer was separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f1a0366dd80646c3afad27ded43aaddc
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989477B2

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