7-Benzoyl-3-methyl-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one → 7-Benzoyl-3-methyl-1,3-dihydro-2H-indol-2-one

HRID 1283627

Reaktionsgleichung

Reaktionsgleichung von HRID 1283627
[C:1]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15](=[O:18])[C:14]2([CH3:21])SC)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Ni].O.O1CCCC1>[C:1]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15](=[O:18])[CH:14]2[CH3:21])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 129098167-Benzoyl-3-methyl-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one

Produkt 1

HCID 129012437-Benzoyl-3-methyl-1,3-dihydro-2H-indol-2-oneAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 444642Hydroxy-nickelKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of 8 g. (0.027 mole) of 7-benzoyl-3-methyl-3-methylthioindolin-2-one in 80 ml. of tetrahydrofuran was treated under N2 with 40 g. of a commercial Raney nickel-water mixture over a 2 hr. period. At the end of this period the mixture was filtered and the residue washed thoroughly with tetrahydrofuran. One drop of concentrated hydrochloric acid was added to the filtrate and the dark orange solution turned pale yellow. The solution was stripped under vacuum to a yellow oil which crystallized on seeding. The material was recrystallized from toluene petroleum ether to give a white crystalline material. The solid (6.0 g., 89% yield) melted at 125°-127°C.

Aufarbeitung

  1. filtrationAt the end of this period the mixture was filtered
  2. washthe residue washed thoroughly with tetrahydrofuran
  3. additionOne drop of concentrated hydrochloric acid was added to the filtrate
  4. customcrystallized on seeding
  5. customThe material was recrystallized from toluene petroleum ether
  6. customto give a white crystalline material

Quellen und Nachweise

ORD-Eintrag
ord-2419da8c6f854bf785a0c2641970523d
Quelldatensatz
uspto-grants-1976_08
Patentnummer
US03975531

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