Methyl 4-methoxyacetoacetate → HCID 178496286, Verbindung

HRID 1805531

Reaktionsgleichung

[F:1][C:2]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][C:3]=1[NH2:4].[N:10]([O-])=O.[Na+].[CH3:14][O:15][CH2:16][C:17](=[O:23])[CH2:18][C:19]([O:21][CH3:22])=[O:20].CC([O-])=O.[Na+]>Cl.O.CCO>[F:1][C:2]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][C:3]=1[NH:4][N:10]=[C:18]([C:17](=[O:23])[CH2:16][O:15][CH3:14])[C:19]([O:21][CH3:22])=[O:20]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a suspension of 2-fluoro-5-iodoaniline (9.83 g, 41.5 mmol) in 6 M HCl aqueous solution (83.0 mL) was added a solution of NaNO2 (3.43 g, 49.8 mmol) in water (8.3 mL) at 0° C. To a suspension of methyl 4-methoxy-3-oxobutanoate (5.37 mL, 41.5 mmol) and NaOAc (124 g) in EtOH (70 mL) was added the above solution at 0° C. The mixture was stirred at 0° C. for 10 min. The precipitates were collected by filtration, washed with water, dissolved in EtOAc, washed with brine, dried over MgSO4, filtered and concentrated in vacuo to yield the title compound (14.2 g, 87% yield) as a red solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 3.31 (3H, s), 3.83 (3H, s), 4.64 (2H, s), 7.03-7.41 (1H, m), 7.43-7.66 (1H, m), 7.85-8.07 (1H, m), 12.20 (1H, brs).

Aufarbeitung

additionwas added the above solution at 0° C
filtrationThe precipitates were collected by filtration
washwashed with water
dissolutiondissolved in EtOAc
washwashed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-44a57e8c78144373930310eda9d9e1d3
Quelldatensatz: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08354411B2

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