Carbon Tetrachloride → HCID 13959041, compound

Participants

Reaction Steps

To 4.3 g of 50 in 1900 ml of carbon tetrachloride a few milligrams of benzoyl peroxide was added, followed by 3.2 g of N-bromosuccinimide and the stirred mixture was refluxed and irradiated with a 200-watt tungsten lamp for 6 hours. The resulting mixture was cooled, washed with water, then with very dilute aqueous sodium bicarbonate solution, dried (MgSO4) and stripped of solvent. The residue (methyl 8-(bromomethyl)cinnoline-4-carboxylate) (58A) was dissolved in 80 ml of acetone, 2.11 g of lithium chloride was added, and the mixture was stirred at room temperature over a weekend. The mixture was stripped of solvent and the residue was dissolved in methylene chloride. The solution was washed with water, dried (MgSO4) and stripped of solvent. The residue was flash chromatographed over silica gel, first using methylene chloride as eluent, then a 1:99 v:v mixture of ethyl acetate and methylene chloride as eluent, to give methyl 8-(chloromethyl)cinnoline-4-carboxylate (58B), as a solid, m.p.: 111°-112° C. (with decomposition).

Provenance & Evidence