Diethyl Ether → Ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-methoxynicotinoyl]acetate

HRID 246941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246941
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:23]=[C:22]([OH:24])[C:21]([F:25])=[CH:20][C:11]=1[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:13].[CH2:26](OCC)C.[N+](=C)=[N-].C(OC(C)C)(C)C>C(OCC)(=O)C.C(O)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:23]=[C:22]([O:24][CH3:26])[C:21]([F:25])=[CH:20][C:11]=1[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:13]

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 7914Diisopropyl EtherHCID 9550DiazomethaneHCID 178472175Ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-hydroxynicotinoyl]acetate

Produkt 1

HCID 15596920Ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-methoxynicotinoyl]acetateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In 2 ml of ethyl acetate was dissolved 100 mg of ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-hydroxynicotinoyl]acetate, and a diethyl ether solution containing 15 mg of diazomethane was added thereto with ice-cooling, after which the resulting mixture was subjected to reaction at room temperature for 30 minutes. Subsequently, acetic acid was added to the reaction mixture until foaming was not caused in the reaction mixture. The solvent was then removed by distillation under reduced pressure and to the crystalline material thus obtained was added 2 ml of diisopropyl ether, after which crystals were collected by filtration to obtain 80 mg (yield 77.0%) of ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-methoxynicotinoyl]acetate. The physical properties of this compound were identical with those of the compound obtained in Example 18.

Aufarbeitung

  1. additionwas added
  2. temperaturewith ice-cooling
  3. customafter which the resulting mixture was subjected to reaction at room temperature for 30 minutes
  4. customThe solvent was then removed by distillation under reduced pressure and to the crystalline material
  5. customthus obtained
  6. filtrationafter which crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-35f65d73c7a04c69aff27345a9539562
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04704459

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