Nabumetone → 4-(5-Bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one

HRID 1290337

Reaktionsgleichung

Reaktionsgleichung von HRID 1290337
[CH3:1][C:2](CCC1C=CC2C=C(OC)C=CC=2C=1)=[O:3].[C:18]([C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:32][CH3:33])[C:27]=2[Br:31])[CH:22]=1)(=[O:20])[CH3:19]>>[Br:31][C:27]1[C:26]([O:32][CH3:33])=[CH:25][CH:24]=[C:23]2[C:28]=1[CH:29]=[CH:30][C:21]([C:18]([OH:20])=[CH:19][C:2](=[O:3])[CH3:1])=[CH:22]2

Komponenten

3

Edukt 2

HCID 4409NabumetoneHCID 6221781-(5-Bromo-6-methoxynaphthalen-2-yl)ethan-1-one

Produkt 1

HCID 701794054-(5-Bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one

Versuchsvorschrift

New process for the synthesis of the antiinflammatory drug known as nabumetone that consists in reacting 2-acetyl-5-bromo-6-methoxynaphthalene with an alkyl acetate in presence of an alkaline alcoholate to get 4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one that by catalytic hydrogenation in a polar solvent and in presence of a base gives 4-(6-methoxy-2-naphthyl)butan-2-one known as nabumetone.

Aufarbeitung

  1. customNew process for the synthesis of the antiinflammatory drug

Quellen und Nachweise

ORD-Eintrag
ord-37bfe041c442425998114372078aa3dc
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750793

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