HCID 19093470, compound → HCID 19093455, compound

Participants

Reaction Steps

A 500 mL r.b. flask containing 1 g of methyl 2-[3-bromophenyl]nicotinate and 30 g of polyphosphoric acid with a stirring bar was dipped in an oil bath at 210° C. While the contents were being warmed, house vacuum (~30 mmole) was slowly applied. After 15 mins., the reaction mixture started to stir easily and slowly started turning orange. This reaction mixture was stirred at 210° and 30 mm pressure for 4 hrs. The flask was taken out and while it was still warm, ~50 g of ice was cautiously added to the reaction mixture. After cooling the stirring reaction mixture to 0°, 60 mL of 5N sodium hydroxide was added slowly over 3 mins. The resulting green solid was filtered and washed thoroughly with 5×25 mL of water. This crude solid was taken up in methylene chloride and applied on silica gel and eluted with 1:20 ethyl acetate:hexane mixture to give a 1:2 ratio of 6-bromo-4-aza-9-fluorenone and 8-bromo-4-aza-9-fluorenone as yellow solids. ##STR18##

Provenance & Evidence