Hydrochloric Acid → HCID 178496282, Verbindung

HRID 1624628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1624628
[N:1]([O-])=O.[Na+].[CH2:5]([O:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([F:20])[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[CH3:22][O:23][CH2:24][C:25](=[O:31])[CH2:26][C:27]([O:29][CH3:30])=[O:28].CC([O-])=O.[Na+]>O.CO>[CH2:5]([O:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][N:1]=[C:26]([C:25](=[O:31])[CH2:24][O:23][CH3:22])[C:27]([O:29][CH3:30])=[O:28])=[C:15]([F:20])[CH:14]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 123500Methyl 4-methoxyacetoacetateHCID 517045Sodium AcetateHCID 114998094-(Benzyloxy)-2-fluoroanilineHCID 23668193Sodium Nitrite

Produkt 1

HCID 178496282HCID 178496282, VerbindungAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of NaNO2 (2.07 g, 30 mmol) in H2O (5 mL) was added dropwise at 0° C. to a mixture of 4-(benzyloxy)-2-fluoroaniline (5.43 g, 25 mmol) and 6 M HCl aqueous solution (25 mL, 150 mmol). After stirring for 15 min, the resulting aqueous solution was added to a suspension of methyl 4-methoxyacetoacetate (3.24 mL, 24 mmol) and NaOAc (12.3 g, 150 mmol) in MeOH (50 mL) pre-cooled at 0° C. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was recrystallized from hexane/AcOEt to give the title compound (8.48 g, 91% yield) as a yellow solid: 1H NMR (300 MHz, CDCl3): δ ppm 3.500 (3H×0.46, s), 3.502 (3H×0.54, s), 3.88 (3H×0.54, s), 3.92 (3H×0.46, s), 4.65 (2H×0.46, s), 4.68 (2H×0.54, s), 5.06 (2H×0.54, s), 5.07 (2H×0.46, s), 6.75-6.86 (2H, m), 7.32-7.44 (5H, m), 7.53 (1H×0.46, t, J=9.0 Hz), 7.76 (1H×0.54, t, J=9.0 Hz), 13.12 (1H×0.46, brs), 15.13 (1H×0.54, brs).

Aufarbeitung

  1. extractionextracted with AcOEt
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from hexane/AcOEt

Quellen und Nachweise

ORD-Eintrag
ord-b3fd40016a99465b87895763cb455ff4
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778944B2

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