Potassium Carbonate → Ethyl 6-iodo-1-(2-morpholinoethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2243053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2243053
F[C:2]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:3]=1[C:4]([C:6](=[CH:12][NH:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[I:26][C:23]1[CH:22]=[C:3]2[C:2](=[CH:25][CH:24]=1)[N:13]([CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[CH:12]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:4]2=[O:5]

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 178472024HCID 178472024, Verbindung2×

Produkt 1

HCID 59208337Ethyl 6-iodo-1-(2-morpholinoethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of ethyl 2-(2-fluoro-5-iodobenzoyl)-3-(2-morpholinoethylamino)acrylate (Intermediate 23, 358 mg, 0.75 mmol) and potassium carbonate (208 mg, 1.50 mmol) in DMF (7 mL) was heated to 100° C. for 4 h. The reaction mixture was cooled to room temperature, filtered, and concentrated under reduced pressure. The solid that formed was placed under high vacuum overnight (328 mg) to yield the desired product. MS (ESP): 457 (M+H+) for C18H21IN2O4; NMR: 1.28 (t, J=7 Hz, 3H), 2.43 (m, 4H), 2.61 (m, 2H), 3.50 (m, 4H), 4.22 (q, J=7 Hz, 2H), 4.46 (m, 2H), 7.67 (d, J=9 Hz, 1H), 8.05 (m, 1H), 8.50 (s, 1H), 8.63 (s, 1H).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe solid that formed
  4. customwas placed under high vacuum overnight (328 mg)

Quellen und Nachweise

ORD-Eintrag
ord-91e0d13955024ae5b3eab593d6b80b20
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07674801B2

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