Nitric Acid → HCID 20061086, compound

Participants

Reaction Steps

2-bromopyridine (3.3 ml) was dissolved in 30 ml of ether and added with 22.1 ml of butyllithium (1.6 M, in hexane) drop by drop at -30° C. To this mixture were added a solution of 5.0 g of 4-chlorobenzonitrile in ether (10 ml) drop by drop at the same temperature. The reaction mixture was stirred for 1 hour and then poured into ice water. Ether was removed in vacuo. The resultant water-layer fraction was acidified by adding 6 N HCl, stirred at 100° C. for 1 hour, cooled, alkalized by adding sodium hydroxide and then extracted with ether. The resultant ether-layer fraction was concentrated and the oil thus obtained was dissolved in 10 ml of fuming sulfuric acid at 0° C. To this solution, added 1.2 ml of fuming nitric acid drop by drop and the resultant solution was stirred at the same temperature for 1 hour. The reaction mixture was poured into ice water and crystals formed were collected by filtration. The crystals were further recrystallized using ethanol, and 3.6 g of crystalline 2-chloro-5-(2-pyridinecarbonyl)nitrobenzene was thus obtained.

Provenance & Evidence