3-Chloro-1-butene → HCID 10036173, compound

Participants

Reaction Conditions

Reaction Steps

A 250 mL round bottom flask was charged with 2.00 g (12.5 mmol) of 2-amino-8-hydroxyquinoline, 3.46 g (25.0 mmol), of K2CO3 and 63 mL of anhydr ethanol. Following the dissolution of 2-amino-8-hydroxyquinoline, 1.51 mL of 3-chloro-1-butene (15.0 mmol) was added in one portion, and the mixture was heated to 65° C. in an oil bath. After 48 h, the solvent was evaporated and the residue dissolved in EtOAc and washed with H2O. The combined aqueous layers were back-extracted with EtOAc. The organic layers were then pooled, dried, and filtered. The residue was then purified by column chromatography (SiO2; EtOAc/hexanes with 0.1% Et3N). The resultant material was then re-crystallized from Et2O to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.82 (m, 1H), 7.16 (m, 1H), 7.00 (m, 2H), 6.73 (m, 1H), 6.39 (m, 2H), 5.67–5.98 (m, 2H), 4.44–4.67 (m, 2H), 1.74 (m, 3H); MS (DCI/NH3) m/z 215 [M+H]+.

Provenance & Evidence