Nitrobenzene → HCID 21257364, compound

Participants

Reaction Steps

A mixture of compound 13 (11.2 g, 58.6 mmol), carbon disulfide (220 mL) and nitrobenzene (80 mL) in a RBF was treated with AlCl3 (38.93 g, 293 mmol) followed by tigloyl chloride (8.33 g, 70.3 mmol). After completion of reaction (TLC chloroform:methanol, 9:1, Rf=0.4) the reaction was worked up as described for preparation of compound 4 and further treatment with triethylamine (8.2 mL, 64.4 mmol) in chloroform (200 mL) as described for 4 gave a residue after work up. The residue on purification by column chromatography (silica gel, 60-120 mesh, chloroform : methanol, 19:1) furnished (±) 5-hydroxy4,8,9-trimethyl-1,8,9,10-tetrahydro-2H-pyrano[2,3-h]-quinoline-2,10-dione (15, 1.9 g) in 21% yield as a solid. M.P. 300° C.

Provenance & Evidence