3-(Nitromethyl)-1,2-dihydronaphthalene → 1,2,3,4-Tetrahydronaphthalen-2-ylmethanamine

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Reaction Steps

2-Nitromethyl-3,4-dihydronaphthalene (XXXV) (25 g) and 20% Pd/C (1.0 g) were combined in MeOH (200 ml) and shaken in a Parr hydrogenator at 3 atmospheres hydrogen pressure for 24 hours, by which time the theoretical amount of hydrogen (4 equivalents) had been absorbed. Removal of the catalyst and solvent left an oil (24 g) which was converted to its HCl salt by solution in MeOH and addition of concentrated HCl. The product, compound XXXI.HCl, was recrystallized from 2-propanol, yielding a white solid, m.p. 230° (dec.). Its elemental analysis and NMR spectrum were consistent with the structure indicated.

Provenance & Evidence