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Sodium Hydroxide → 1-Oxo-1,3-dihydroisobenzofuran-6-carbaldehyde oxime

HRID 1766873
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1766873
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]=O)[CH:9]=2)[CH2:4][O:3]1.Cl.[NH2:14][OH:15].[OH-].[Na+]>>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]=[N:14][OH:15])[CH:9]=2)[CH2:4][O:3]1
KomponentenVersuchsvorschriftQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 178625183-Oxo-1,3-dihydroisobenzofuran-5-carbaldehyde

Produkt 1

HCID 734121851-Oxo-1,3-dihydroisobenzofuran-6-carbaldehyde oxime

Versuchsvorschrift

According to a similar procedure to that described in Example 4-(4), 1-oxo-1,3-dihydroisobenzofuran-6-carbaldehyde (2.42 g, 14.9 mmol) obtained from Example 5-(1), hydroxylamine hydrochloride (1.35 g, 19.4 mmol), and an aqueous solution of sodium hydroxide (1.0N; 19.3 ml, 19.3 mmol) were reacted, and the reaction mixture was worked up to afford 1-oxo-1,3-dihydroisobenzofuran-6-carbaldehyde oxime as a crude solid. According to a similar procedure to that described in Example 4-(4), the crude product obtained above, triethylamine (3.92 g, 39 mmol), and anhydrous trifluoroacetic acid (4.08 g, 19.4 mmol) were reacted, and the reaction mixture was worked up to afford, after extraction and concentration, a solid residue. The residue was subjected to chromatography on a silica gel (50 g) column (eluent; ethyl acetate:dichloromethane=0:1˜1:10) to afford the title compound (1.67 g, 70% yield) as a solid (mp. 195-196° C.).

Quellen und Nachweise

ORD-Eintrag
ord-adc1702eb8084071b5b7ded78bea7cb5
Quelldatensatz
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07230023B2

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