Hydrochloric Acid → 5-amino-2-[4-(3-chloropropylamino)-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-one

HRID 1736122Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1736122
C([N:4]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[C:25]([F:26])=[CH:24][C:23]([F:27])=[C:22]([NH2:28])[C:18]=3[C:19](=[O:21])[CH:20]=2)=[CH:11][C:10]=1[F:29])[CH2:5][CH2:6][CH2:7][Cl:8])(=O)C.Cl.O>O1CCOCC1>[NH2:28][C:22]1[C:18]2[C:19](=[O:21])[CH:20]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([NH:4][CH2:5][CH2:6][CH2:7][Cl:8])=[C:10]([F:29])[CH:11]=3)[O:16][C:17]=2[C:25]([F:26])=[CH:24][C:23]=1[F:27]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 19434902HCID 19434902, Verbindung

Produkt 1

HCID 194348465-amino-2-[4-(3-chloropropylamino)-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-oneAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

508 mg (1.20 mmol) of the resulting 2-[4-[N-acetyl-N-(3-chloropropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one was dissolved in 30 ml of dioxane, 30 ml of concentrated hydrochloric acid was added and the mixture was stirred for 3 hours under heating at reflux. The reaction solution was cooled on ice and adjusted to pH 8 by addition of water thereto, and the precipitated crystals were collected by filtration. The crystals were purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give 224 mg (49%) of 5-amino-2-[4-(3-chloropropylamino)-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-one.

Aufarbeitung

  1. temperatureunder heating
  2. temperatureat reflux
  3. temperatureThe reaction solution was cooled on ice
  4. filtrationthe precipitated crystals were collected by filtration
  5. customThe crystals were purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-99abc3c764c647b1a8ef37c5409fb541
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05539112

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