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 1704326

Reaktionsgleichung

Reaktionsgleichung von HRID 1704326
[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>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

3

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 1

HCID 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 nickelwater 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-ecc835171d4e47e59a71ca986af1d4bc
Quelldatensatz
uspto-grants-1978_11
Patentnummer
US04126635

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