Dimethylformamide dimethyl acetal → Methyl 1-(2-fluoro-5-iodophenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylate

HRID 1407171

Reaktionsgleichung

Reaktionsgleichung von HRID 1407171
[F:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[NH:9][N:10]=[C:11]([C:16](=[O:20])[CH2:17][O:18][CH3:19])[C:12]([O:14][CH3:15])=[O:13].[CH3:21]OC(OC)N(C)C>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[N:9]1[CH:21]=[C:17]([O:18][CH3:19])[C:16](=[O:20])[C:11]([C:12]([O:14][CH3:15])=[O:13])=[N:10]1

Komponenten

3

Edukt 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178496286HCID 178496286, Verbindung

Produkt 1

HCID 59436288Methyl 1-(2-fluoro-5-iodophenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylateAusbeute 78 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of methyl 2-[(2-fluoro-5-iodophenyl)hydrazono]-4-methoxy-3-oxobutanoate (14.2 g, 35.9 mmol) in N,N-dimethylformamide dimethyl acetal (142 mL) was heated to reflux for 1.5 h and cooled to 0° C. The precipitates were collected by filtration, washed with hexane and dried to yield the title compound (11.3 g, 78% yield) as a pale yellow solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 3.80 (3H, s), 3.82 (3H, s), 7.37 (1H, dd, J=10.6, 8.7 Hz), 7.90-8.01 (1H, m), 8.14 (1H, dd, J=7.2, 2.3 Hz), 8.55 (1H, s).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with hexane
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-238f4b8915944df8a0ab6ced451ab3a3
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916566B2

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