Process for preparing isocoumarins
AssigneeIlex Products, Inc.
InventorsWilliam E. Bauta, William R. Cantrell, Jr., Dennis P. Lovett
Life of this patent
Estimating the term…
Abstract
The present invention provides a process from preparing isocoumarin-3-yl derivatives comprising reacting a homophthalic anhydride derivative with a carbonyl compound, wherein the carbonyl group is substituted with an acyl activating group, in the presence of a reaction medium comprising a solvent and a base. The invention also encompasses a process for the preparation of homophthalate esters useful in the preparation of homophthalic anhydride reactants as well as an integrated process wherein the twp reactions are carried out sequentially to afford the desired isocoumarin derivative.
Claims26
A process for the preparation of isocoumarin derivatives of the formula
- wherein R1 and R2 are independently H, halogen, C1-C6 alkyl, C1-C6 alkenyl, C1-C6 alkynyl, aryl, heteroaryl, C1-C6 acyl, C1-C6 alkoxyl, —NR4R5, wherein when R4 is H then R5 is sulphonyl or C1-C6 acyl or where R4 and R5 are independently C1-C6 alkyl or C1-C6 acyl;
- and R3 is an electron withdrawing group;
- X is a substituent selected from halo, C1-C6 alkyl, C1-C6 alkenyl, C1-C6 alkynyl, aryl, heteroaryl, C1-C6 acyl, C1-C6 alkoxyl, —NR4 R5, wherein R5 and R4 are as defined above, or SO2R6, where R6 is C1-C6 alkyl or C1-C6 acyl;
- and n is an integer from 0 to 4, wherein when n is greater than 1 the X substituents may be the same or different;
- comprising reacting a homophthalic anhydride of the formula
- wherein R1, X and n are as defined above;
- with a carbonyl compound of the formula
- wherein R2 and R3 are as defined above;
- and Y is an acyl activating substituent;
- in the presence of a reaction medium comprising a solvent and a base.
A process for the preparation of isocoumarin derivatives of the formula:
- wherein R11 and R12 are independently C1-C6 alkyl;
- and R9 and R10 are independently C1-C6 alkyl or C1-C6 alkoxy;
- comprising reacting a homophthalic anhydride of the formula:
- wherein R9 and R10 are as defined above;
- with a carbonyl compound of the formula:
- wherein R11 and R12 are as defined above;
- and Y is an acyl activating group;
- in the presence of a reaction medium comprising a solvent and a base.
Dependencies are inferred from the claim text.