3-(1,3-Dioxolan-2-yl)-2-hydrazino-7-methylquinoline

In the title molecule, C13H15N3O2, the dihedral angle between the mean plane of the 1,3-dioxolane group and the 2-hydrazino-7-methylisoquinoline unit is 85.21 (5)°. The conformation of the molecule is influenced by bifurcated N—H⋯(O,O) and N—H⋯N intramolecular hydrogen bonds. In the crystal structure, molecules are linked via intermolecular N—H⋯O hydrogen bonds, forming extended chains along [001].

In the title molecule, C 13 H 15 N 3 O 2 , the dihedral angle between the mean plane of the 1,3-dioxolane group and the 2-hydrazino-7-methylisoquinoline unit is 85.21 (5) . The conformation of the molecule is influenced by bifurcated N-HÁ Á Á(O,O) and N-HÁ Á ÁN intramolecular hydrogen bonds. In the crystal structure, molecules are linked via intermolecular N-HÁ Á ÁO hydrogen bonds, forming extended chains along [001].

Comment
The title compound (I), belongs to the quinoline class. Quinolines and quinolinones are an integral part of many naturally occurring fused heterocycles and find application in synthetic and pharmaceutical chemistry (Kametani, 1968).
Isoquinolinones and isoquinolineamines have been reported as cancer chemotherapeutic agents (Behrens, 1999) whereas quinolyl and isoquinolyl derivatives have been reported as insecticidal compounds (Broadhurst, 1991). 3-substituted isoquinolines have potent use in medicine (Chao et al., 1999) and in general, hydrazine derivatives can be used as medicaments (Broadhurst et al., 2001;Choudhury, et al., 2002;Choudhury & Guru Row, 2006;Yang, et al., 2008). Due to the importance of quinoline derivates (Cho et al., 2002) and in continuous of our research on quinolines and isoquinoline derivatives (Hathwar et al., 2008;Manivel et al., 2009) we present here crystal structure of the title compound.
In (I) the dihedral angle between 1,3-dioxolane moiety and 2 hyrazino-7-methyl isoquinoline unit is 85.21 (5)°. All bond lengths (Allen et al., 1987) and angles are within normal ranges. The conformation of the molecule is influenced by N-H···O and N-H···N intramolecular hydrogen bonds whereas the crystal structure is stabilized by intermolecular N-H···O hydrogen bonds forming exteded chains along [001].

Experimental
A solution of 2-chloro (3-(1,3-dioxolan-2-yl)-7-methylquinoline in ethanol was treated with hydrazine hydrate and stirred at 323 K for 3hr. The product was filtered. The solid was washed with water and diethyl ether and dried under vacuum.
Single crystals were obtained by recrystalization of (I) from DMSO.

Refinement
All H atoms positioned geometrically and refined using a riding model with bond lengths C-H = 0.93 Å (for aromatic), 0.97 Å (for methylene) and 0.96 Å (for methyl). The U iso (H) = 1.5U eq (C) for methyl and U iso (H) = 1.2U eq (C) for all other carbon bound H atoms. H atoms bonded to N atoms were located in difference Fourier maps and refined isotropically.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.