Hydrochloric Acid → methyl 2-[(4-bromo-2,5-difluorophenyl)hydrazinylidene]-4-methoxy-3-oxobutanoate

HRID 1624692

Reaktionsgleichung

Reaktionsgleichung von HRID 1624692
[N:1]([O-])=O.[Na+].[Br:5][C:6]1[C:12]([F:13])=[CH:11][C:9]([NH2:10])=[C:8]([F:14])[CH:7]=1.Cl.[CH3:16][O:17][CH2:18][C:19](=[O:25])[CH2:20][C:21]([O:23][CH3:24])=[O:22].CC([O-])=O.[Na+]>O.CO>[Br:5][C:6]1[C:12]([F:13])=[CH:11][C:9]([NH:10][N:1]=[C:20]([C:19](=[O:25])[CH2:18][O:17][CH3:16])[C:21]([O:23][CH3:24])=[O:22])=[C:8]([F:14])[CH:7]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 123500Methyl 4-methoxyacetoacetateHCID 517045Sodium AcetateHCID 27732854-Bromo-2,5-difluoroanilineHCID 23668193Sodium Nitrite

Produkt 1

HCID 178496284methyl 2-[(4-bromo-2,5-difluorophenyl)hydrazinylidene]-4-methoxy-3-oxobutanoateAusbeute 105,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of NaNO2 (7.9 g, 115 mmol) in H2O (20 mL) was added dropwise at 0° C. to a mixture of 4-bromo-2,5-difluoroaniline (20 g, 96 mmol) and 6 M HCl aqueous solution (96 mL, 576 mmol). After stirring for 15 min, the resulting aqueous solution was added to a suspension of methyl 4-methoxyacetoacetate (12.4 mL, 96 mmol) and NaOAc (34 g, 576 mmol) in MeOH (165 mL) pre-cooled at 0° C. The precipitate was collected by filtration, washed with water and dried at room temperature to give the title compound (37 g, 100% yield) as a red solid: 1H NMR (300 MHz, DMSO-d6): δ ppm 3.34 (3H, s), 3.83 (3H, s), 4.68 (2H, s), 7.70 (1H, dd, J=9.7, 7.0 Hz), 7.89 (1H, dd, J=10.6, 6.1 Hz), 12.16 (1H, s).

Aufarbeitung

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-b92395b0d8ca4c4294d289e454875add
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778944B2

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