1- Cyano-2-methoxynaphthalene

A first step involves the preparation of 2-Cyano-6-methoxynaphthalene (cyanonerolin). 

Illumination of 1-methoxynaphthalene in media containing cyanide ion gives a good yield of l-cyano-4-methoxynaphthalene (and very little 1-cyanonaphthalene) whereas photocyanation of naphthalene itself proceeds with only small yields (Lok and Havinga, 1974). 

Al-Jalal reported that the photocycloaddition of l-cyano-4-methoxynaph-thalene with alkenes commonly occurs at the 1,2 bonds of the naphthalene ring [126,131], However, when 2-cyano-6-methoxynaphthalene (52) was treated with 2-chloroacrylonitrile, ( )-ethoxyacrylonitrile, or ( )-cinnamonitrile, the (2 + 2) cycloadducts showed a different regiochemistry [132,133] (Scheme 21). Irradiation of 52 in the presence of ethyl vinyl ether or ( )-dichloroethene did not give a cross-adduct, but gave a photodimer of 52. 

A first step involves the preparation of 2-cyano-6-methoxynaphthalene (cyanonerolin). 90 g of 2-bromo-6-methoxynaphthalene are heated with 60 g of cuprous cyanide in a metal bath at 240° to 250°C stirring for one hour. At the instant when the cuprous cyanide begins to react and dissolves, the mass turns brown, liquefies and heats up strongly. The molten mass is poured onto a cold surface, is pulverized and sifted. This powder is treated with dilute ammonia (1 liter of water to 300 cc of commercial ammonia solution). The solution is filtered on a Buchner filter and the precipitate that remains on the filter is washed with dilute ammonia and then with water. 

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