Sodium Carbonate → N-(4-(4-Aminonaphthalen-1-yloxy)pyridin-2-yl)-2-methoxyacetamide

HRID 593420Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 593420
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([N+:24]([O-])=O)=[CH:16][CH:15]=2)[CH:10]=[CH:9][N:8]=1)=[O:5].C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.[Fe]>[NH2:24][C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([O:13][C:11]2[CH:10]=[CH:9][N:8]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][O:2][CH3:1])[CH:12]=2)=[CH:15][CH:16]=1

Komponenten

5

Edukt 2

HCID 10340Sodium CarbonateHCID 674524762-Methoxy-N-(4-(4-nitronaphthalen-1-yloxy)pyridin-2-yl)acetamide

Produkt 1

HCID 66718180N-(4-(4-Aminonaphthalen-1-yloxy)pyridin-2-yl)-2-methoxyacetamideAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A stirred suspension of 2-methoxy-N-(4-(4-nitronaphthalen-1-yloxy)pyridin-2-yl)acetamide (11) (44.0 g, 125 mmol) and iron powder (41.7 g, 747 mmol) in acetic acid (300 mL) was heated at 45° C. After 3 hr the mixture was cooled to RT and poured slowly and cautiously onto solid Na2CO3 (200 g). The mixture effervesced vigorously. The mixture was partitioned between water (500 mL) and EtOAc (500 mL). The aqueous layer was basified with solid Na2CO3 to pH 11 and filtered through a pad of celite. The aqueous layer and celite pad were extracted with EtOAc (3×500 mL) and the combined extracts were washed with saturated aqueous NaHCO3 solution (500 mL), dried (MgSO4) and evaporated in vacuo to afford N-(4-(4-aminonaphthalen-1-yloxy)pyridin-2-yl)-2-methoxyacetamide (12) (35.0 g, 78%) as a purple foam: m/z 324 (M+H)+ (ES+).

Aufarbeitung

  1. temperatureAfter 3 hr the mixture was cooled to RT
  2. customThe mixture was partitioned between water (500 mL) and EtOAc (500 mL)
  3. filtrationfiltered through a pad of celite
  4. extractionThe aqueous layer and celite pad were extracted with EtOAc (3×500 mL)
  5. washthe combined extracts were washed with saturated aqueous NaHCO3 solution (500 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-209f554b95544ca18ca18eb3b3b5b7be
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242960B2

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