Water → HCID 18472450, Verbindung

HRID 566122Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566122
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([N:6]([CH2:8][CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH3:7])=[C:4]([CH:20]=O)[CH:3]=1.C(O[K])(C)(C)C.O>C(O)(C)(C)C>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([CH3:7])[CH2:8][CH2:9][C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:20][C:4]=2[CH:3]=1.[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([CH3:7])[CH2:8][CH2:9][C:10]([C:11]([OH:13])=[O:12])=[CH:20][C:4]=2[CH:3]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 18472651tert-butyl 4-(4-bromo-2-formyl-N-methylanilino)butyrateHCID 178418922HCID 178418922, Verbindung

Produkt 2

HCID 184722637-bromo-1-methyl-2,3-dihydro-1H-1-benzoazepine-4-carboxylic acidAusbeute 17 %HCID 18472450HCID 18472450, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

In tert-butanol (250 ml) was dissolved tert-butyl 4-(4-bromo-2-formyl-N-methylanilino)butyrate (4.54 g) and tert-butoxy potassium (1.43 g), and the mixture was refluxed for 1 hour and cooled. To the mixture was added water (500 ml), and the mixture was extracted with ethyl acetate (500 ml×2). The aqueous layer was made weakly acidic with 1N hydrochloric acid (about 12.5 ml), and the mixture was extracted with ethyl acetate (500 ml). Both of these organic layer was washed with saturated brine (250 ml) and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified with silica gel column chromatography (200 g, hexane:ethyl acetate=10:1→1:1) to give tert-butyl 7-bromo-1-methyl-2,3-dihydro-1-benzoazepine-4-carboxylate (3.33 g, 77%) and 7-bromo-1-methyl-2,3-dihydro-1H-1-benzoazepine-4-carboxylic acid (0.60 g, 17%).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperaturecooled
  3. extractionthe mixture was extracted with ethyl acetate (500 ml×2)
  4. extractionthe mixture was extracted with ethyl acetate (500 ml)
  5. washBoth of these organic layer was washed with saturated brine (250 ml)
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified with silica gel column chromatography (200 g, hexane:ethyl acetate=10:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-f3e66335d8cb49acb961fd4efe2cf5ed
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172061B2

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