Preparation of tetrahydroquinolines and related compounds
US4526970A · kind A · utility
Assignee
Inventor
Key dates
| Filing date | Jun 21, 1983 |
| Grant date | Jul 2, 1985 |
| Priority date | — |
| Expiry date | Jun 21, 2003 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07F7/10
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
An improved process for preparing tetrahydroquinolines and related compounds especially 5,6,7,8-tetrahydroquinoline-8-nitriles, amides and thioamides is described. The nitriles and thioamides are anti-ulcer and/or anti-secretory agents. Typically a compound of formula A ##STR1## where M is sodium, potassium, lithium or MgHal where Hal is chlorine, bromine or iodine, is reacted, e.g., in an ether solvent, with a silyl compound R.sub.x.sup.a Si(NCY).sub.4-x (III) wherein R.sup.a is alkyl, cycloalkyl, aralkyl, or aryl, at least one group R.sup.a being a branched chain alkyl, cycloalkyl, aryl or branched chain aralkyl, Y is oxygen or sulphur, x has a value from 1 to 3, then subjecting the product to hydrolysis or alcoholysis, to obtain the corresponding nitrile, amide or thioamide, provided that when a nitrile is desired the molar ratio of compound III to compound A is at least 2:1 and x is 3 and Y is S. The products may be obtained as acid addition salts. Compound A may contain various substituents, e.g., hydrocarbon substituents. Some compounds of formula III are novel and are also claimed.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.