3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile

Preparation of 3, 4-dimethoxy-bicyclo[4.2.0]octa-l, 3, 5-triene-7-carbonitrile (III)In a 250 ml flask in argon atmosphere 50 ml of anhydrous tetrahydrofuran was added. The mixture was cooled to -10 °C and 33 ml of 2.5 M butyllithium hexane solution was added 25 dropwise while the temperature was kept below-10 °C. Then the reaction was stirred for 10 minutes at -10°C. 13.0 ml of diisopropylamine (or 10.0 ml diethylamine) was added dropwise while the temperature was kept at -10°C.Then the reaction was stirred for 10 minutes. 10.0 g of 3-(2-bromo-4, 5-dimethoxy- phenyl)-propionitrile (II) dissolved in 30 ml of anhydrous tetrahydrofuran was added30 dropwise to the solution at -10 °C. The reaction was stirred at -10 °C.After the reaction had been completed it was allowed to warm up to 0 °C and 100 ml of 1 M hydrochloric acid was added dropwise while the temperature was kept below 20 °C. After 5 minutes stirring the phases were separated. The aqueous phase was washed twice with 50 ml of toluol. The combined organic phases were washed with 1x50 ml of 1 M hydrochloric acid and 1x50 ml of saturated sodium chloride solution.The organic phase was evaporated in vacuum to 20 g. 20 ml of ethanol was added to the residue and it was evaporated in vacuum again to 20 g. 30 ml of ethanol was added to the residue and it was evaporated again to 20 g.The residue was stirred on ice-water. The product was crystallized, it was stirred for 30 minutes at 0-5 °C. Then it was filtered and washed with ethanol. It was dried in vacuum at 40 °C.5.55 g of the title compound was obtained in 80percent yield.Based on Tetrahedron 1973, 29, pp 73-76 EXAMPLE 4 3, 4-dimethoxybicyclo[4.2.0]octa-1, 3, 5-triene-7-carbonitrile Based on Tetrahedron 1973, 29, pp 73-76 To a solution of NaNHBased on Tetrahedron 1973, 29, pp 73-76 [0035] To a solution of NaNHStep 5: Example 3 4.5-Dimethoxy-l-cyano-benzo cyclobutane (50gm) was dissolved in a Flask containing Tetrahydrofuran (750 ml) at room temperature followed by the addition of 40% of Monomethyl amine (40gm) solution in Tetrahydrofuran (250 ml) and 10% Pd/C of 50% wet (l5gm). Hydrogen 4-5kgswas applied and the reaction was stirred for 16 hours at room temperature. After completion of reaction, the resultant mass was filtered through Hyflow bed and distilled the solvent under vacuum to obtain the crude 3, 4-Dimethoxy n-methyl bicyclo [4.2.0] octa-l, 3, 5-triene-7- methanamine. (0122) Recovery of Palladium Carbon: l3gms (0123) Yield: 91%A study using a number of bacterial inducers (propionitrile, benzonitrile, 4-bromobenzonitrile) showed that propionitrile provided the best induction of nitrilase activity with Weigh the nitrilase being studied (15 mg), in the form of a lyophilisate, into a tube and then add 4 ml of 0.1M KH2PO4 buffer pH=7 and Weigh the nitrilase being studied (15 mg), in the form of a lyophilisate, into a tube and then add 4 ml of 0.1M KH2PO4 buffer pH=7 and

4,5-Dimethoxy-1-cyanobenzocyclobutane is used in the preparation of selective bradycardic agents.

Molecular Weight:189.21
XLogP3:0.6
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:189.078978594
Monoisotopic Mass:189.078978594
Topological Polar Surface Area:42.2
Heavy Atom Count:14
Complexity:257
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes