Hydrochloric Acid → HCID 20496460, compound

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Reaction Steps

2.605 g of 2-pentyl-1,2,3,4-tetrahydro-naphthalene-6-carboxamide are suspended in 40 ml of absolute pyridine and treated with 2.86 g of benzenesulfonyl chloride while stirring. The solution, which becomes clear, is left to stand at room temperature overnight, the poured into a mixture of 50 g of ice and 40 ml of concentrated hydrochloric acid and exhaustively extracted with dichloromethane. The organic phases are washed neutral with water, dried over sodium sulfate and the solvent is removed by evaporation in vacuo. There are obtained 2.390 g of crude 2-pentyl-1,2,3,4-tetrahydronaphthalene-6-carbonitrile as a yellowish oil which, for purification, is chromatographed on 90 g of silica gel. Elution with hexane/toluene (1:1) and toluene yields 2.35 g of a yellowish oil which crystallizes at -10° C. It is crystallized up to a constant melting point from a small amount of ethanol by cooling the solution to -10° C. and separating the mother liquor from the precipitated crystals, for example, by decantation, pipetting or filtration through a cooled filter. Subsequently, it is dried up to constant weight in a high vacuum (0.01 mbar). There are obtained colorless crystals, or a colorless oil, of 2-pentyl-1,2,3,4-tetrahydronaphthalene-6-carbonitrile; m.p. 18.2° C.

Provenance & Evidence