Ciba-geigy Corporation

Claus D Weis

Peter Sutter

Maurice Grelat

Karl Schaffner

Alex Meisels

Jean Claude Roger

A process for the preparation of alkali metal salts of phosphonic acid monoalkyl esters of formula ##STR1## by reacting 1 mole of a phosphonic acid ester of formula ##STR2## with 1 mole of a finely particulate alkali metal halide of formula XY. In these formulae, R is straight chain or branched C.sub.1 -C.sub.20 alkyl, R.sub.1 is C.sub.1 -C.sub.4 alkyl, X is an alkali metal cation and Y is a halogen anion.

Process for the preparation of alkali metal salts of phosphonic acid

Metal salts of phosphoric and phosphonic acid esters of formula ##STR1## wherein R is C.sub.1 -C.sub.4 alkoxy or straight chain or branched unsubstituted C.sub.1 -C.sub.20 alkyl or C.sub.2 -C.sub.6 alkenyl,

Process for the preparation of metal salts of phosphoric and phosphonic

A process is described for the preparation of compounds of the formula ##STR1## in which R and X are as defined in claim 1. The compounds of the formula (1) are valuable intermediates in the synthesis of triarylmethane dyes and triarylmethanelactones.

Process for the preparation of substituted pyridines

There are disclosed benzanthrone lactones of formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined in claim 1. The benzanthrone lactones of formula (1) are important intermediates for the synthesis of novel dyes which are obtained by coupling suitable diazo components to said compounds of formula (1).

Benzanthrone lactones

A process for the manufacture of 4,5-dichloro-2-(4-chlorophenoxy)phenol by selective chlorination of 2-phenoxyanisole with 3 to 5 molar equivalents of chlorine, in the temperature range between -10.degree. and +50.degree. C., preferably between 0.degree. and 30.degree. C., in a lower halogenated aliphatic hydrocarbon, a lower aliphatic nitrile, in dimethyl formamide, dimethylmethanephosphonate or methanol, preferably in dimethyl formamide, dimethylmethanephosphonate, methanol, acetonitrile, propionitrile, chloroform, methylene chloride, 1,2-dichloroethane or tetrachloroethane, and demethylation of the 4,5-dichloro-2-(4-chlorophenoxy)anisole obtained as intermediate with an acid.

Process for the manufacture of 4,5-dichloro-2-(4-chlorophenoxy)phenol

Substituted N-methylbenzoxazines of the formula ##STR1## wherein the ring A can also contain a nitrogen atom as ring member, each of R.sub.1 and R.sub.3 independently is hydrogen, lower alkyl, halogen, nitro or trifluoromethyl, each of R.sub.2 and R.sub.4 independently is hydrogen or halogen and each of m and n is an integer from 1 to 3, are obtained by cyclizing compounds of the formula ##STR2## wherein A, R.sub.2, R.sub.4, m and n are as defined above, R is chlorine or bromine, and each of R.sub.1 ' and R.sub.3 ' independently is hydrogen, lower alkyl, halogen or trifluoromethyl, in the presence of dimethylmethanephosphonate, at reflux temperature, and, if desired, nitrating the resultant compounds.

Process for the production of substituted N-methylbenzoxazines

A novel process for producing 2,3,5,6-tetrachloropyridine is described. In this process, pentachloropyridine is reacted, in an alkanephosphonic acid dialkyl ester (dialkyl alkane phosphonate) having 1 to 4 carbon atoms in each of the alkyl groups or in a phosphoric acid trialkyl ester (trialkyl phosphate) having 1 to 4 carbon atoms in each of the alkyl groups as the solvent, at 60.degree. to 120.degree. C., in the presence of 1.4 to 2.8 mols, per mol of pentachloropyridine, of an ammonium salt of an inorganic or organic acid, with 1.2 to 1.6 gram atoms of zinc per mol of pentachloropyridine, with selective dechlorination of the pentachloropyridine in the 4-position occurring. 2,3,5,6-Tetrachloropyridine is a valuable commercial product, which can be used for producing insecticidal formulations. Furthermore, 2,3,5,6-tetrachloropyridine is used as intermediate for the production of herbicidally effective .alpha.-[4-(3',5',6'-trichloropyrid-2'-yloxy)-phenoxy]-alkanecarboxylic acids and derivatives thereof. There are also described novel ammonium salts of methanephosphonic acid monomethyl ester, in the presence of which the selective dechlorination of pentachloropyridine in the 4-position can be advantageously performed.

Process for producing 2,3,5,6-tetrachloropyridine

A novel process for producing 2,3,5-trichloropyridine is described. In this process, 2,3,4,5-tetrachloropyridine is reacted, in an alkanephosphonic acid dialkyl ester (dialkyl alkane phosphonate) having 1 to 4 carbon atoms in each of the alkyl groups or in a phosphoric acid trialkyl ester (trialkyl phosphate) having 1 to 4 carbon atoms in each of the alkyl groups as the solvent, at 60.degree. to 120.degree. C., in the presence of 1.4 to 2.8 mols, per mol of 2,3,4,5-tetrachloropyridine, of an ammonium salt of an inorganic or organic acid, with 1.2 to 1.6 gram atoms of zinc per mol of 2,3,4,5-tetrachloropyridine, the 2,3,4,5-tetrachloropyridine being selectively dechlorinated in the 4-position. 2,3,5-Trichloropyridine is a valuable intermediate for producing herbicidally effective .alpha.-[4-(3',5'-dichloropyrid-2-yloxy)-phenoxy-]-alkanecarboxylic acids and derivatives thereof. There are also described novel ammonium salts of methanephosphonic acid monomethyl ester, in the presence of which salts the selective dechlorination of 2,3,4,5-tetrachloropyridine in the 4-position is advantageously performed.

Process for producing 2,3,5-trichloropyridine

The invention provides a process for the production of alkoxy-substituted polycyclic aromatic compounds from corresponding hydroxy-substituted compounds.

Process for the production of alkoxy-substituted polycyclic aromatic

Phenylalkyl sulphones of the formula ##STR1## wherein R represents hydrogen, halogen or alkyl of 1 to 4 carbon atoms, R.sub.1 represents alkyl of 1 to 4 carbon atoms, and R.sub.2 represents hydrogen, and, if R is hydrogen, or alkyl, also represents nitro, Are obtained by reaction of a corresponding sulphinic acid derivative or a salt thereof with a dialkyl alkanephosphonate.

Process for the production of phenylalkyl sulphones

Compounds of the class of spiro[norbornane-2,3'-piperidines], spiro[bicyclo[2.2.2]octane-2,3'-piperidines], and corresponding spiro-pyrrolidine derivatives which are unsubstituted at the ring nitrogen atom or substituted by neutral or basic radicals, and the pharmaceutically acceptable acid addition salts of these new compounds possess valuable pharmacological properties and are active ingredients for pharmaceutical compositions. In particular, these new compounds have an antiviral activity. Specific embodiments are (1RS,2RS,4SR)-spiro[norbornane-2,3'-piperidine]-hydrochloride and 1'-[2-(2-azaspiro[5.5]undec-2-yl)-ethyl]-spiro[bicyclo[2.2.2]octane-2,3'-p iperidine]-dihydrochloride.

Growing community of inventors

Pfeffingen, Switzerland

Claus D Weis