Potassium Carbonate → 7-Chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester

HRID 1887815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887815
[CH3:1][O:2][C:3](=[O:24])[C:4]([N:6]([C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20](=[O:23])[CH2:21][CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][O:2][C:3]([C:4]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]2[C:14]([C:20](=[O:23])[C:21]=1[CH3:22])=[CH:15][CH:16]=[C:17]([Cl:19])[CH:18]=2)=[O:24]

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 70816656Methyl (n-(5-chloro-2-propionylphenyl)-N-phenylcarbamoyl)formate

Produkt 1

HCID 708166537-Chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl esterAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A stirred suspension of N-(5-chloro-2-propionyl-phenyl)-N-phenyl-oxalamic acid methyl ester (15.0 g, 43.5 mmol) in methanol (200 mL) was treated with potassium carbonate (35.0 g, 253 mmol) at 25° C. The mixture was then heated at 80° C. for 1 hr. At this time, the reaction was cooled to 25° C. The resulting solids were collected by filtration through a sintered glass funnel and then washed with methanol (2×50 mL). The filtrate was concentrated in vacuo. The resulting residue was dissolved in ethyl acetate (500 mL) and was washed with water (2×200 mL). The organics were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting solids were triturated with hexanes and diethyl ether to afford 7-chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (10.5 g, 73.4%). 1H NMR (DMSO-d6) δ ppm 8.24 (d, J=8.7 Hz, 1H) 7.28-7.78 (m, 6H) 6.69 (d, J=1.7 Hz, 1H) 3.49 (s, 3H) 1.97 (s, 3H). MS calcd. for C18H14ClNO3 [(M+H)+] 328.0 found 327.9.

Aufarbeitung

  1. temperatureAt this time, the reaction was cooled to 25° C
  2. filtrationThe resulting solids were collected by filtration through a sintered glass funnel
  3. washwashed with methanol (2×50 mL)
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionThe resulting residue was dissolved in ethyl acetate (500 mL)
  6. washwas washed with water (2×200 mL)
  7. dry with materialThe organics were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting solids were triturated with hexanes and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f4909a6b8e4b4b37ac8e115d9c719d03
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501732B2

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