Potassium Hydroxide → 1-(4-Butylbenzyl)isoquinoline

HRID 1673077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1673077
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][N:14]=2)=O)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].O.NN.[OH-].[K+]>C(O)COCCO>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][N:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 17851496(4-Butylphenyl)(isoquinolin-1-yl)methanone

Produkt 1

HCID 99002251-(4-Butylbenzyl)isoquinolineAusbeute 55,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8117Diethylene GlycolLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

The compound of Example B3 (1.7 g, 6.0 mmol), hydrazine monohydrate (836 mg, 17 mmol), and potassium hydroxide (769 mg, 14 mmol) were added to diethylene glycol (8.5 ml), and this mixture was stirred at 80° C. for 1 hour, at 160° C. for 3.5 hours, then at 200° C. for 1 hour. The mixture was cooled to room temperature, ice water was added, and this was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (914 mg).

Aufarbeitung

  1. waitat 200° C. for 1 hour
  2. temperatureThe mixture was cooled to room temperature
  3. extractionthis was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-840baf8155de4df99243456e11883772
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07999090B2

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