Sulfuric Acid → 2-chloro-8,9-dihydro-10-methylpyrido[1,2-a]indol-6(7H)-one

HRID 486183Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486183
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[CH3:11][CH:12]1[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][C:13]1=O.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[Cl:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[N:9]1[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][C:13]1=[C:12]2[CH3:11]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 709452-Methyl-1,3-cyclohexanedioneHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)

Produkt 1

HCID 103539602-chloro-8,9-dihydro-10-methylpyrido[1,2-a]indol-6(7H)-oneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
82.5 °C

Versuchsvorschrift

To a suspension of p-chlorophenylhydrazine hydrochloride (8.52 g) in toluene (100 ml) were added 2-methylcyclohexane-1,3-dione (5.0 g) and 40% sulfuric acid (40 ml), and the mixture was stirred at 80-85° C. for 4 hours. After cooling, the organic layer was separated. The aqueous layer was extracted with toluene. The organic layers were combined and washed with aqueous sodium bicarbonate, water, and brine. After dried over sodium sulfate, the organic layer was evaporated. The residue was recrystallized from methanol to give 2-chloro-8,9-dihydro-10-methylpyrido[1,2-a]indol-6(7H)-one (4.63 g).

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with toluene
  4. washwashed with aqueous sodium bicarbonate, water, and brine
  5. dry with materialAfter dried over sodium sulfate
  6. customthe organic layer was evaporated
  7. customThe residue was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-2e52c32915dd405ea0771bfe9e44394c
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290785

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