Tetrahydrofuran → 5-Chloro-3-hydroxy-3-(2-methoxyphenyl)indolin-2-one

HRID 965527

Reaktionsgleichung

Reaktionsgleichung von HRID 965527
[Mg:1].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2=[O:22].C1[CH2:27][O:26]CC1>CCOCC.O>[CH3:27][O:26][C:12]1[CH:13]=[CH:14][CH:18]=[CH:19][C:20]=1[Mg:1][Br:2].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2([OH:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10]

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 113582-BromoanisoleHCID 872035-chloro-1H-indole-2,3-dioneHCID 5462224Magnesium

Produkt 2

HCID 219059555-Chloro-3-hydroxy-3-(2-methoxyphenyl)indolin-2-oneHCID 178489560HCID 178489560, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 2-methoxyphenylmagnesium bromide is prepared from 1.35 g of magnesium and 10.5 g of 1-bromo-2-methoxybenzene in 100 ml of ether. This solution is added in 10 minutes at RT, under an argon atmosphere, to a mixture of 4.1 g of 5-chloroisatin and 70 ml of THF. After stirring for 1 hour at RT, water is added and the product is filtered off, redissolved in THF, dried over magnesium sulfate and evaporated under vacuum in the presence of iso ether. The residue is chromatographed on silica using a DCM/AcOEt mixture (60/40; v/v) as the eluent to give the expected product after crystallization from a THF/iso ether mixture. m=3.7 g. M.p.=235°-238° C.

Aufarbeitung

  1. filtrationthe product is filtered off
  2. dissolutionredissolved in THF
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under vacuum in the presence of iso ether
  5. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (60/40; v/v) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-f65128a08d1d4eeb9cdfadf235707307
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05773612

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