Hydrochloric Acid → (2,3-Dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone

HRID 1943670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943670
[F:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][C:15]3[CH:19]=[CH:20][N:21]=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([F:10])[C:7]=1[O:8]C.[Br-].[Li+].N1CCNCC1.Cl>O.CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][C:15]3[CH:19]=[CH:20][N:21]=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([F:10])[C:7]=1[OH:8].[O:16]1[CH2:17][CH2:18][N:13]([CH:11]=[O:12])[C:14]2[CH:22]=[N:21][CH:20]=[CH:19][C:15]1=2

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 82050Lithium BromideHCID 44608224(3,5-Difluoro-4-methoxy-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone

Produkt 2

HCID 44608225(3,5-Difluoro-4-hydroxy-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanoneHCID 86650558(2,3-Dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanoneAusbeute 231,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a 10 ml flask, (3,5-difluoro-4-methoxy-phenyl)-(2,3-dihydro -pyrido[4,3-b][1,4]oxazin-4-yl)-methanone (50 g, 0.163 mmol), lithium bromide (57 mg, 0.65 mmol) and piperazine (21 mg, 0.24 mmol) were dissolved with N,N-dimethyl formamide, and stirred at 1000 for 3 hours. After completion of the reaction by adding water dropwise, the mixture was adjusted to weak acidic condition (pH=6) by using 1N hydrochloric acid, and the formed solid was filtered and washed with distilled water and ethyl acetate. The resulting solid was recrystallized from methanol to obtain the target compound 29, i.e., 3,5-difluoro-4-hydroxy -phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone (31 mg, 65%).

Aufarbeitung

  1. customAfter completion of the reaction
  2. filtrationthe formed solid was filtered
  3. washwashed with distilled water and ethyl acetate
  4. customThe resulting solid was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-3f85de2900224204a8f0a4993c156fee
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394792B2

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