Hoechst Celanese Corporation

Other

Napp Technologies

Mohammad Aslam

Kenneth G Davenport

Richard Vicari

Ralph R Dammel

Juergen Lingnau

Karl-Friedrich Doessel

George Kvakovszky

Michael T Sheehan

Wilson B Ray

Brad L Smith

Daniel A Aguilar

Charles B Hilton

Debasish Kuila

William Basinger

James R Sounik

Graham N Mott

Varadaraj Elango

Ranjit C Desai

Joseph A McDonough

John R Durrwachter

Humberto Ramos, Jr

Douglas J Gordon

Henry C Linstid, Iii

Hans-Joachim Metz

Charles H Brown, Ii

Ibrahim M Uwaydah

Sharon R Fitzhenry

Joel C Smith

Dora E Rios

John F Fritch

Nicholas Gallegos

A novel process is disclosed for the preparation of dihydropyridine compounds and derivatives thereof, and more particularly felodipine. The process to prepare felodipine involves a two step procedure condensing 2,3-dichlorobenzaldehyde with methyl acetoacetate in the presence of a catalyst system. The resultant benzylidine intermediate is sequentially reacted with ethyl aminocrotonate to provide felodipine. The novelty of the present invention resides in part on (1) a new catalyst system not previously disclosed for the preparation of felodipine, (2) the absence of acid(s), (3) the control of reaction conditions to yield lower amounts of unreacted aldehyde compared to known reactions, (4) a simplified purification process, and (5) formation of negligible quantities of symmetrical diester byproducts.

Process to prepare dihydropyridine and derivatives thereof

A novel process for preparing sulfonic acid esters and amides of benzo-heterocyclic diazo diketo compounds, such as substituted diazo-4-oxo-3,4-dihydrocoumarins, which are useful synthetic intermediates in a wide variety of applications including photoresists, opto-electronics, agricultural, and pharmaceutical applications is disclosed and claimed. The process comprises the steps of (a) subjecting a substituted benzo-heterocyclic .beta.-keto-enol compound to suitable diazo transfer conditions in the presence of a diazo transfer agent; (b) subjecting the so formed diazo diketo compound to suitable halosulfonation conditions in the presence of a halosulfonation agent; and (c) subjecting the so formed halosulfonyl aromatic compound to suitable substitution reaction in the presence of an alcohol or an amine to form the corresponding sulfonic acid ester or amide of benzo-heterocyclic diazo diketo compound. The compounds formed from the process of the present invention exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.

Process for preparing coumarin sulfonates

A new class of 3-diazo-3,4-dihydrocoumarin compounds which are useful as photoactive compounds in a wide variety of applications including photoresists and other opto-electronic applications are disclosed and claimed. Preferred embodiments include 6-sulfonyl-3-diazo-4-oxo-3,4-dihydrocoumarin esters. These compounds exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.

Photoactive coumarin sulfonate compounds

A new class of 3,4-dihydrocoumarin derivatives which are useful as photoactive compounds in a wide variety of applications including photoresists and other opto-electronic applications are disclosed and claimed. Preferred embodiments include ether, ester, carbonate, and sulfonate derivatives of 5-hydroxy, 6-hydroxy, and 7-hydroxy-3-diazo-4-oxo-3,4-dihydrocoumarins. These compounds exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.

Photoactive coumarin derivatives

Novel processes for the preparation of a new class of coumarin derivatives, which are useful as photoactive compounds in a wide variety of applications including photoresists and other opto-electronic applications, are disclosed and claimed. The process involves a multi-step synthetic method for the preparation of ether, ester, carbonate, or sulfonate derivative of 5-hydroxy, 6-hydroxy, or 7-hydroxy-3-diazo-4-oxo-3,4-dihydrocoumarin starting from the corresponding dihydroxyacetophenone. The compounds formed from the process of the present invention exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.

Process for preparing photoactive coumarin derivatives

The present invention provides processes which are flexible, cost effective, and commercially viable methods of manufacturing or producing products from 2-hydroxyacetophenone (2-HAP). Of particular interest of the available products are 4-hydroxycoumarin, warfarin-alkali salt, preferably warfarin sodium and warfarin-alkali salt-isopropyl alcohol (2-propanol) complex, more preferably warfarin-sodium-isopropyl alcohol complex. As is known, these compounds are useful as vitamin K dependent anticoagulants in the treatment of humans and animals. In different doses, they are also useful as rodenticide. The inventive process involves contacting 2-HAP, carbonate ester and effective base followed by treatment with an unsaturated ketone and phase transfer catalyst to ultimately yield product.

Syntheses based on 2-hydroxyacetophenone

Substituted phenethanol ethers are prepared in useful yields by the etherification of corresponding substituted phenethyl alcohols with aliphatic primary alcohols. The etherification is carried out by reacting a substituted phenethyl alcohol with an aliphatic primary alcohol in the presence of an acid catalyst at a temperature of at least about 75.degree. C.

Process for preparing phenethanol ethers

The palladium-catalyzed coupling of aryl and vinyl halides with vinylic compounds is disclosed. A preferred embodiment relating to the palladium catalyzed coupling of 4-substituted and 6-substituted-2-methoxynaphthalene to form nabumetone is also disclosed. The beauty of this novel reaction is that methylvinylketone, normally employed by the art directly as-is for the preparation of nabumetone, is formed in situ. We have discovered a mechanism to take advantage of the in situ formation of methylvinylketone, thus avoiding the use of expensive, toxic, and unstable methyl vinyl ketone feed. This reaction may be employed for a variety of pharmaceutically active and non-pharmaceutical compounds.

Use of 4-substituted 2-butanones to prepare nabumetone

The present invention provides a unique and novel way of producing carbinols such as 4-hydroxyphenylmethylcarbinol (HPMC). In this new process, a ketone such as 4-hydroxyacetophenone (4-HAP) is heated under suitable hydrogenation conditions of temperature and pressure in the presence of a suitable catalyst and a basic material, and for a sufficient period of time to form HPMC.

Process for preparing 4-hydroxyphenylmethylcarbinol

Novel 4-substituted acetophenone anils and methods for preparing 1,3,5-tris(4'-hydroxyphenyl)benzenes from 4-substituted acetophenones such as 4-hydroxyacetophenones or, from substituted 4-hydroxyacetophenone-anils such as 4-hydroxyacetophenone-anil by reacting the 4-substituted acetophenone or corresponding anil with an aniline derivative.

Process for the preparation of 1,3,5-tris(4'-hydroxyaryl)benzene

Process for the prepartion of 1,3,5-tris(4'-hydroxyaryl)benzene

A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.

Process for the preparation of substituted styrenes

An intermediate for the manufacture of nabumetone, 4-(6'-methoxy-2'-naphthyl)-3-buten-2-one, is prepared by contacting 2-bromo-6-methoxynaphphalene with methyl vinyl ketone in the presence of a palladium catalyst at from about 50.degree. C. to about 200.degree. C. for a time sufficient to cause substantially complete reaction to occur.

Preparation of 4-(6'-methoxy-2'-naphthyl)-3-buten-2-one

Process for the preparation of bisarylalkyl ethers

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Corpus Christi, TX, United States of America

Mohammad Aslam