Diethyl Malonate → Ethyl 2-(3-chloro-2,4-difluorobenzoyl)-3-ethoxy-acrylate

HRID 1953234

Reaktionsgleichung

Reaktionsgleichung von HRID 1953234
ClC1C(F)=C(C=CC=1F)C(Cl)=O.C(OCC)(=O)CC(OCC)=O.[Cl:24][C:25]1[C:26]([F:45])=[C:27]([CH:41]=[CH:42][C:43]=1[F:44])[C:28]([CH:30]([C:36]([O:38][CH2:39][CH3:40])=O)[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:29].ClC1C(F)=C(C=CC=1F)C(CC(OCC)=O)=O.C([O-])([O-])OCC.C(OC(=O)C)(=O)C>>[Cl:24][C:25]1[C:26]([F:45])=[C:27]([CH:41]=[CH:42][C:43]=1[F:44])[C:28]([C:30](=[CH:36][O:38][CH2:39][CH3:40])[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:29]

Komponenten

6

Edukt 5

HCID 7761Diethyl MalonateHCID 27735383-Chloro-2,4-difluorobenzoyl chlorideHCID 22077280Diethyl (3-chloro-2,4-difluorobenzoyl)malonateHCID 54232984Ethyl (3-chloro-2,4-difluoro-benzoyl)-acetateHCID 86583744Ethyl orthoformate acetic anhydride

Produkt 1

HCID 54286793Ethyl 2-(3-chloro-2,4-difluorobenzoyl)-3-ethoxy-acrylate

Versuchsvorschrift

Reaction of 3-chloro-2,4-difluoro-benzoyl chloride with diethyl malonate gives diethyl (3-chloro-2,4-difluoro-benzoyl)-malonate, and partial hydrolysis and decarboxylation lead to ethyl (3-chloro-2,4-difluoro-benzoyl)-acetate, which is reacted with ethyl orthoformate/acetic anhydride to give ethyl 2-(3-chloro-2,4-difluorobenzoyl)-3-ethoxy-acrylate; further reaction with cyclopropylamine leads to ethyl 2-(3-chloro-2,4-difluoro-benzoyl)-3-cyclopropylaminoacrylate, which is cyclized with potassium carbonate/dimethylformamide to give ethyl 8-chloro-1-cyclopropyl-7-fluoro-1,4-dihydro-4-oxo-3 -quinolinecarboxylate; hydrolysis then finally leads to the corresponding carboxylic acid. The reaction sequence described can be represented by the following equation: ##STR4##

Aufarbeitung

  1. customgives

Quellen und Nachweise

ORD-Eintrag
ord-82e41766b79e4d9185eb8ecebe068678
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06114590

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