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Hydrochloric Acid → Ethyl 7-bromo-1-formyl-2,3-dihydro-1-benzazepine-4-carboxylate

HRID 566143
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 566143
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([N:6]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[O:8])=[C:4]([CH:19]=O)[CH:3]=1.CC(C)([O-])C.[K+].O.Cl>C(O)(C)(C)C>[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([CH:7]=[O:8])[CH2:9][CH2:10][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:19][C:4]=2[CH:3]=1.[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([CH:7]=[O:8])[CH2:9][CH2:10][C:11]([C:12]([OH:14])=[O:13])=[CH:19][C:4]=2[CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21715711ethyl 4-(4-bromo-2,N-diformylanilino)butyrateHCID 23665647Potassium tert-butoxide

Produkt 2

HCID 18472216Ethyl 7-bromo-1-formyl-2,3-dihydro-1-benzazepine-4-carboxylateAusbeute 22 %
HCID 18472517
7-Bromo-1-formyl-2,3-dihydro-1-benzazepine-4-carboxylic acid
Ausbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

In t-butanol (500 ml) were dissolved ethyl 4-(4-bromo-2,N-diformylanilino)butyrate (15.32 g) and potassium t-butoxide (5.53 g), and the mixture was refluxed for 30 minutes. To the mixture were added water (500 ml) and 1N hydrochloric acid (50 ml), and the mixture was extracted with ethyl acetate (1000 ml). The organic layer was washed with saturated brine (200 ml) and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified with silica gel column chromatography (300 g, hexane:ethyl acetate=4:1→1:1) to give ethyl 7-bromo-1-formyl-2,3-dihydro-1-benzazepine-4-carboxylate (3.13 g, 22%) and 7-bromo-1-formyl-2,3-dihydro-1-benzazepine-4-carboxylic acid (1.39 g, 10%).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 30 minutes
  2. extractionthe mixture was extracted with ethyl acetate (1000 ml)
  3. washThe organic layer was washed with saturated brine (200 ml)
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified with silica gel column chromatography (300 g, hexane:ethyl acetate=4:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-bf374e104b1346d0a6c29df6dccf8ee2
Quelldatensatz
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06172061B2

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