Hydrochloric Acid → 1-(4-chlorobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine

HRID 1360554

Reaktionsgleichung

Reaktionsgleichung von HRID 1360554
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10]([C:22]#[N:23])=[N:11][N:12]([CH2:19][CH2:20][CH3:21])[C:13]=1[CH2:14][CH2:15][CH2:16][CH2:17][Cl:18]>C(O)C>[Cl:18][CH2:17][CH2:16][CH2:15][CH2:14][C:13]1[N:12]([CH2:19][CH2:20][CH3:21])[N:11]=[C:10]2[C:9]=1[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[N:2]=[C:22]2[NH2:23]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 669588824-(2-aminophenyl)-5-(4-chlorobutyl)-1-propyl-1H-pyrazole-3-carbonitrile

Produkt 1

HCID 577175341-(4-chlorobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amineAusbeute 63,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

Hydrochloric acid (18 mL, 71.0 mmol) in ethanol was added dropwise to a solution of 4-(2-aminophenyl)-5-(4-chlorobutyl)-1-propyl-1H-pyrazole-3-carbonitrile (7.50 g, 23.7 mmol) in 150 mL of ethanol. The resultant solution was heated to reflux overnight, concentrated under reduced pressure, and diluted with water. The pH of the mixture was adjusted to 9-10 by slow addition of solid sodium carbonate. The aqueous layer was extracted with several portions of dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford a reddish solid. The material was purified via flash column chromatography on silica gel (eluting with a 96:4 mixture of dichloromethane/methanol) to afford 4.78 g of 1-(4-chlorobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine.

Aufarbeitung

  1. temperatureto reflux overnight
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with water
  4. additionThe pH of the mixture was adjusted to 9-10 by slow addition of solid sodium carbonate
  5. extractionThe aqueous layer was extracted with several portions of dichloromethane
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto afford a reddish solid
  11. customThe material was purified via flash column chromatography on silica gel (
  12. washeluting with a 96:4 mixture of dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-406860c1a3494857b8df1203262b0dff
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879849B2

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