The quinoline fused-ring system of the title compound, C11H 8ClNO, is planar (r.m.s. deviation = 0.005 Å); the formyl group is slightly bent out of the plane [C- C- C-O1 torsion angles = 8.8 (7) and-172.8 (4)°].

Nawaz Khan F

Department of Chemistry

School of Advanced Sciences

Vellore Campus

Dr.Subashini Rajagopal

VIT Business School

Chennai Campus

Kushwaha A.K

Hathwar V.R

Ng S.W.

Fulltext

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2-Chloro-8-methyl­quinoline-3-carbaldehyde

Acta Crystallographica Section E Structure Reports Online

AbstractThe Mitsunobu reaction is a well-established fundamental reaction and has been widely applied in organic synthesis. In this paper, under Mitsunobu conditions dehydration proceeds between (2-chloroquinolin-3-yl)methanol and nitrogen heterocyclic compounds such as quinazolinone, pyrimidone, 2-oxoquinoline in dry THF in the presence of triethylamine, triphenylphosphane and diethyl azodicarboxylate to give the corresponding products. As part of our recent research, we attempted to couple two N-heterocyclic compounds under Mitsunobu reaction conditions to provide efficient building blocks for natural product synthesis.

Chemical Papers

Regioselective N-alkylation of (2-chloroquinolin-3-yl) methanol with N-heterocyclic compounds using the Mitsunobu reagent

The molecule of title compound, C11H10ClNO, is close to being planar (r.m.s deviation for the non-H atoms = 0.017 Å). In the crystal, molecules inter-act by way of O-H⋯O hydrogen bonds, generating C(2) chains propagating in [010]. The crystal structure is consolidated by C-H⋯π inter-actions and aromatic π-π stacking inter-actions [centroid-centroid distance = 3.661 (2) Å].

(2-Chloro-8-methylquinolin-3-yl)methanol

2-Chloro-8-methylquinoline-3-carbaldehyde

Journal	Acta Crystallographica Section E Structure Reports Online
Publisher	International Union of Crystallography (IUCr)
ISSN	16005368
Open Access	0