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US 4,358,593 AGranted
Process for preparing 3-(4-aminoethoxybenzoyl)benzo[b]thiophenes
AssigneeEli Lilly and Company
InventorsCharles D. Jones, Mary E. Goettel
Life of this patent
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Abstract
The use of particularly advantageous protecting groups for the hydroxy groups of 6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophenes provides a high-yielding process for the preparation of such compounds having a 4-(2-aminoethoxy)benzoyl 3-group.
Claims19
A process for preparing a compound of the formula ##STR8## wherein R.sup.1 and R.sup.2 are independently C.sub.1 -C.sub.4 alkyl, or combine to form C.sub.4 -C.sub.6 polymethylene or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --;
- which process comprises acylating a compound of the formula ##STR9## wherein R is --COR.sup.3 or --SO.sub.2 CH.sub.3, and R.sup.3 is methyl, phenyl, p-tolyl, p-anisyl, or mono- or di(halo or nitro)phenyl;
- under Friedel-Crafts conditions with an acylating agent of the formula ##STR10## wherein R.sup.5 is X or ##STR11## X is chloro, bromo or --SO.sub.2 R.sup.3 ;
- and R.sup.4 is chloro, bromo, iodo, or an activating ester group;
- when R.sup.5 is X, displacing the X group with an amine of the formula ##STR12## and cleaving the R groups.
1 more element
Dependencies are inferred from the claim text.