Indole-3-Butyric Acid → 4-(2-oxo-2,3-dihydro-1H-indol-3-yl)butanoic acid

HRID 743148

Reaktionsgleichung

Reaktionsgleichung von HRID 743148
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:2]1.CS(C)=[O:18].Cl.[N+](=C)=[N-]>>[O:18]=[C:2]1[CH:3]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1]1

Komponenten

4

Edukt 3

HCID 8617Indole-3-Butyric AcidHCID 9550DiazomethaneHCID 12206146DMSO HCl

Produkt 1

HCID 27640884-(2-oxo-2,3-dihydro-1H-indol-3-yl)butanoic acidAusbeute 89 %

Versuchsvorschrift

Similar treatment of methyl 3-(3-indolinyl)propanoic [II: R1 =R3 =H, R2 =(CH2)2COOH] (0.93 g) with DMSO/HCl, followed by esterification with diazomethane and chromatography on silica gel, gave methyl 3-(2-oxo-3-indolyl)propanoate [III: R1 -R3 =H, R2 =(CH2)2COOMe] (0.89 g, 89%) as a yellow oil (Julian PL, Printy HC, J. Am. Chem. Soc. 1953;75:5301-5305 report mp 79°-80° C.).

Quellen und Nachweise

ORD-Eintrag
ord-501ac1cf53b0410397480cd85e89fd5d
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556874

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