Ammonium Chloride → Ethyl 1-(4-fluorophenyl)-4-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 1662025

Reaktionsgleichung

Reaktionsgleichung von HRID 1662025
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11](=[C:17]([CH3:19])[CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])=[CH:4][CH:3]=1.[CH3:20]OC(OC)N(C)C.[NH4+].[Cl-]>CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:20]=[CH:19][C:17]([CH3:18])=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]2=[O:10])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 78373Dimethylformamide dimethyl acetalHCID 66767015Ethyl 2-(4-fluorophenylcarbamoyl)-3-methylbut-2-enoate

Produkt 1

HCID 66767143Ethyl 1-(4-fluorophenyl)-4-methyl-2-oxo-1,2-dihydropyridine-3-carboxylateAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of ethyl 2-(4-fluorophenylcarbamoyl)-3-methylbut-2-enoate (1.85 g, 6.97 mmol) and N,N-dimethylformamide dimethyl acetal (5 mL, 37.45 mmol) is stirred at 90° C. for 90 min. After the reaction is cooled, EtOAc (30 mL) and saturated NH4Cl solution (20 mL) are added. The organic phase is separated, dried and concentrated. The residue is purified by silica gel column chromatography eluting with DCM:MeOH (10:1). The fractions containing product are concentrated, and the residue is mixed with ether to give 1.2 g of yellow solid which is filtered and discarded. The filtrate is concentrated and purified again by silica gel column chromatography eluting with DCM:MeOH (20:1) to give the product (500 mg, 26% yield). MS (m/z): 276.1 (M+H).

Aufarbeitung

  1. temperatureAfter the reaction is cooled
  2. customThe organic phase is separated
  3. customdried
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel column chromatography
  6. washeluting with DCM:MeOH (10:1)
  7. additionThe fractions containing product
  8. concentrationare concentrated
  9. additionthe residue is mixed with ether

Quellen und Nachweise

ORD-Eintrag
ord-b4bec93afae042889ba97f088d11eea0
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030302B2

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