Trifluoroacetic acid → 1-(4-chlorobutyl)-2-propyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-amine

HRID 2283879

Reaktionsgleichung

Reaktionsgleichung von HRID 2283879
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]([CH2:20][CH2:21][CH3:22])[N:8]=[C:9]2[C:18]=1[C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:11]=[C:10]2[NH2:19].FC(F)(F)C(O)=O.[OH-].[K+]>ClCCl.[Pt]=O>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]([CH2:20][CH2:21][CH3:22])[N:8]=[C:9]2[C:18]=1[C:17]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=1[N:11]=[C:10]2[NH2:19]

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 577175341-(4-chlorobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine

Produkt 1

HCID 669583401-(4-chlorobutyl)-2-propyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-amineAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1-(4-chlorobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine (19.45 g, 61.39 mmol), prepared as described in Example 46, platinum oxide (10.00 g) and trifluoroacetic acid (200 mL) was placed under hydrogen pressure (50 psi, 3.4×105 Pa) for 2 days. The reaction mixture was filtered through CELITE filter aid. The filtrate was concentrated under reduced pressure to provide a dark oil. The oil was chilled in an ice bath, ice was added, and the mixture was made basic (pH 14) by the addition of 1 N potassium hydroxide. The resulting solid was isolated by filtration and then dissolved in dichloromethane. The solution was washed sequentially with 1 N potassium hydroxide, water, and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was dried under vacuum for 2 days to provide 18.0 g of 1-(4-chlorobutyl)-2-propyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-amine as an oil.

Aufarbeitung

  1. customprepared
  2. customfor 2 days
  3. filtrationThe reaction mixture was filtered through CELITE
  4. filtrationfilter aid
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto provide a dark oil
  7. temperatureThe oil was chilled in an ice bath
  8. additionice was added
  9. customThe resulting solid was isolated by filtration
  10. washThe solution was washed sequentially with 1 N potassium hydroxide, water, and brine
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was dried under vacuum for 2 days

Quellen und Nachweise

ORD-Eintrag
ord-adc42281179e4009ba26295e74970c66
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145410B2

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