Sodium Hydroxide → (6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-yl)acetic acid

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Reaktionsgleichung

C[O:2][C:3](=[O:24])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:23])[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1.[OH-].[Na+]>CO.C1COCC1>[Cl:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([CH2:4][C:3]([OH:24])=[O:2])=[C:6]([C:15](=[O:23])[C:16]3[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[NH:7]2)=[CH:12][CH:11]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of methyl[6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-yl]acetate (Example 8, 1.80 g) and 2N aqueous NaOH (7.5 ml) in MeOH-THF (10 ml-10 ml) was stirred at 80° C. for 1 h. The mixture was cooled and concentrated. The residue was dissolved in water (150 ml) and washed with diethyl ether (50 ml). The aqueous layer was acidified with 2N aqueous HCl (10 ml), and extracted with ethyl acetate (100 ml×2). The combined organic extracts were washed with brine (50 ml), dried (MgSO4), and concentrated. The residual solids were recrystalized from toluene to afford 1.58 g (91%) of the title compound.

Aufarbeitung

temperatureThe mixture was cooled
concentrationconcentrated
dissolutionThe residue was dissolved in water (150 ml)
washwashed with diethyl ether (50 ml)
extractionextracted with ethyl acetate (100 ml×2)
washThe combined organic extracts were washed with brine (50 ml)
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residual solids were recrystalized from toluene

Quellen und Nachweise

ORD-Eintrag: ord-e3f5642825574b27b621e57f37b843da
Quelldatensatz: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06608070B1

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