Toluene → 2-Butyl-4-(2-methyl-1H-indol-3-yl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

HRID 750681Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 750681
CC[N:3]([CH2:6][CH3:7])[CH2:4][CH3:5].[C:8]([OH:13])(=O)[C:9](O)=O.[CH2:14]([NH:18][NH2:19])[CH2:15][CH2:16][CH3:17].[C:20]1([CH3:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Na+]>CCOC(C)=O>[CH2:14]([N:18]1[N:19]=[C:22]([C:21]2[C:5]3[C:4](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:3][C:6]=2[CH3:7])[CH:23]2[CH:9]([CH2:26][CH:20]=[CH:25][CH2:24]2)[C:8]1=[O:13])[CH2:15][CH2:16][CH3:17]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 162021Butylhydrazine oxalate

Produkt 1

HCID 1363886102-Butyl-4-(2-methyl-1H-indol-3-yl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

The product of step a) (200 mg, 0.71 mmol) was treated with Et3N (0.71 mmol, 98 uL), n-butyl hydrazine oxalate (0.71 mmol, 126 mg) and 10 mL toluene. The suspension was refluxed for 48 h. The reaction was cooled, treated with 15 mL EtOAc and 5 mL 1M NaOH, and heated to 70° C. for 30 min. The organic layer was filtered through silica gel and further eluted with EtOAc. The combined eluent was concentrated to dryness to give the sub-titled compound which was used without further purification.

Aufarbeitung

  1. temperatureThe suspension was refluxed for 48 h
  2. temperatureThe reaction was cooled
  3. filtrationThe organic layer was filtered through silica gel
  4. washfurther eluted with EtOAc
  5. concentrationThe combined eluent was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f25c1de8a58349878a3a0df9ebedfac3
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405215B2

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