Phthalic Anhydride → 2-(3-(Tert-butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide

HRID 242134

Reaktionsgleichung

Reaktionsgleichung von HRID 242134
[C:1]([O:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].NC(N)=[O:23].OO.C1(=O)OC(=O)C2=CC=CC=C12.[O-]S([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.O>[C:1]([O:5][C:6]([C:7]1[CH:8]=[C:9]([C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N+:14]=2[O-:23])[CH:10]=[CH:11][CH:12]=1)=[O:20])([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 5

HCID 6811Phthalic Anhydride2×HCID 10340Sodium CarbonateHCID 24437Sodium Sulfite2×HCID 31294Carbamide PeroxideHCID 57516851tert-Butyl 3-(3-methylpyridin-2-yl)benzoate

Produkt 1

HCID 584883712-(3-(Tert-butoxycarbonyl)phenyl)-3-methylpyridine 1-oxideAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

tert-Butyl-3-(3-methylpyridin-2-yl)benzoate (1.0 eq) is dissolved in EtOAc (6 vol). Water (0.3 vol) is added followed by urea-hydrogen peroxide (3 eq). The phthalic anhydride (3 eq) is added portion-wise as a solid to maintain the temperature in the reactor below 45° C. After completion of phthalic anhydride addition, the mixture is heated to 45° C. After stirring for an additional 4 hours, the heat is turned off. 10% w/w aqueous Na2SO3 (1.5 eq) is added via addition funnel. After completion of Na2SO3 addition, the mixture is stirred for an additional 30 minutes and the layers separated. The organic layer is stirred and 10% w/w aq. Na2CO3 (2 eq) is added. After stirring for 30 minutes, the layers are allowed to separate. The organic phase is washed 13% w/v aq NaCl. The organic phase is then filtered and concentrated to afford crude 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (95%) that is used directly in the next step.

Aufarbeitung

  1. temperatureto maintain the temperature in the reactor below 45° C
  2. stirringthe mixture is stirred for an additional 30 minutes
  3. customthe layers separated
  4. stirringThe organic layer is stirred
  5. stirringAfter stirring for 30 minutes
  6. customto separate
  7. washThe organic phase is washed 13%
  8. filtrationThe organic phase is then filtered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-14658760966142b38c2ab3a529d1d9dd
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653103B2

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