Abstract
The title compound, C20H19NO2, is of inter-est as a precursor to biologically active substituted quinolines and related compounds. This compound crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. The dihedral angles between mean planes of the methyl-phenyl ring and the naphthalene ring system are 78.32 (6) and 84.70 (6)° in mol-ecules A and B, respectively. In the crystal, the anti-ferroelectric packing of mol-ecules A and B is of an ABBAABB type along the b-axis direction. The crystal structure features N-H⋯O, O-H⋯O and weak C-H⋯O hydrogen bonds, which link the mol-ecules into infinite chains propagating along the b-axis direction.
Highlights
The title compound, C20H19NO2, is of interest as a precursor to biologically active substituted quinolines and related compounds
The dihedral angles between mean planes of the methylphenyl ring and the naphthalene ring system are 78.32 (6) and 84.70 (6) in molecules A and B, respectively
The crystal structure features N—HÁ Á ÁO, O—HÁ Á ÁO and weak C—HÁ Á ÁO hydrogen bonds, which link the molecules into infinite chains propagating along the b-axis direction
Summary
1-Aminoalkyl-2-naphthols are used as bradycardiac (Dingermann et al, 2004) and hypotensive agents (Shen et al, 1999). 1,3-oxazines possess pharmaceutical properties such as analgesic (Lesher et al, 1955), antitumor (Remillard et al, 1975), antimalaria (Ren et al, 2001) and antibiotic (Haneishi et al, 1971). The above compounds are prepared from 1-aminoalkyl-2-naphthols (Damodiran et al, 2009) and for this reason they are of great interest. The usual method for the preparation of 1-aminoalkyl-2-naphthols is a three-component reaction between 2-naphthol, aromatic aldehydes and acetamide catalysed by various catalysts (Singh et al, 2015). For our part we propose a new method using phenylboronic acid as catalyst in a free-solvent medium. Symmetry codes: (i) x; y þ 1; z; (ii) x; y À 1; z; (iii) Àx þ 2; Ày þ 1; Àz þ 1
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