SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENEMETHANOLS. II. 1-HALONAPHTHALENES IN THE FRIEDEL AND CRAFTS REACTION¹

Abstract

4-Haloacetonaphthones were needed as starting materials for the synthesis of certain amino alcohols (1). It appeared probable that these could be synthesized most readily by the Friedel and Crafts reaction on halonaphthalenes, and this has proved to be the case. Schweitzer (2) first prepared a bromoacetonaphthone by the reaction of 1-bromonaphthalene, acetyl chloride, and aluminum chloride in carbon disulfide but did not prove the structure of the product. Dziewonski and Stembach (3) carried out the same reaction and showed that 4-bromo-1 -acetonaphthone was the principal product, by oxidation to 4-bromo-1 -naphthoic acid. Other examples of the Friedel and Crafts reaction with 1 -halonaphthalenes have been reported by Mayer and Muller (4) and by Fieser and Desreux (5). The latter found that the reaction between 1 -chloronaphthalene and 4-methylhydrindene-7carboxylic acid chloride failed when excess 1 -chloronaphthalene was used as the solvent, but in tetrachloroethane an 82% yield of a substituted benzanthrone was obtained. No account was taken of isomers present in minor amounts in

1-(Naphthylalkyl)-1H-imidazole derivatives, a new class of anticonvulsant agents

“…Aromatic substitution of ketones 5 and 13 in the synthetically most accessible positions (compounds 6-12, [14][15][16][17][18] gave enhanced activity by the ip route only with certain alkyl substituents (9, 14-16). Furthermore, although oral activity was adversely affected by alkyl groups in the 2-naphthyl series (8,9), substitution of the 1naphthyl ketone 13 with a single alkyl group not only increased activity by the ip route (14-16) but gave a compound (15) comparable in activity to 5 both ip and po. Unfortunately, similar substitution of the ketal 19 (to 23) did not afford the same advantage.…”

Phosphorescence quenching studies of bromoacetonaphthones in solution

“…7. The crude product was isolated in 75% yield as a pale yellow oil that crystallized on standing for several days at O°C.…”

SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENEMETHANOLS. I. AMINO KETONE METHOD1

“…The synthesis of 4-haloacetonaphthones is described in the next paper (9). One trial of Noller and Adams' directions (21) for the synthesis of 2-methoxy-l-acetonaphthone by the Friedel and Crafts reaction between 2-methoxynaphthalene and acetic anhydride gave a low yield, and most of the material used was prepared from acetyl chloride (22) by a procedure involving remethylation of the crude reaction product with dimethyl sulfate before isolation.…”

“…In the case of 4-methoxy-l-chloroacetonaphthone, however, it was easier to prepare the chloro ketone directly by a Friedel and Crafts reaction of 1-methoxynaphthalene and chloroacetyl chloride. The details of the synthesis of the 4-halogen-substituted acetonaphthones are given in a separate paper (9). The reaction of naphthacyl halides with dialkylamines has been reported by Day and co-workers (10,11) in addition to the investigators already mentioned (1, 5, 6) but the instability of the resulting amino ketones has not been emphasized.…”