Methyl iodide → HCID 19045327, compound

Participants

Reaction Steps

A mixture of 1'-acetyl-3,4-dihydro-5-hydroxy-6-nitro-spiro[2H-1-benzopyran-2,4'-piperidine]-4-one (3.84 g, 12 mmol), potassium carbonate (1.66 g, 12 mmol) and methyl iodide (3.74 ml, 8.51 g, 60 mmol) in DMF (30 ml) was stirred in a sealed vessel at room temperature for 3 days, adding further portions of methyl iodide (1 ml) after 24 and 48 h. The solvent was evaporated under reduced pressure, water (60 ml) was added, the pH was adjusted to 6.5 with HCl-H2O (2M) and the mixture was extracted with methylene chloride (3×60 ml). The combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure. The crude product was re-subjected to the above procedure, the solvent was evaporated under reduced pressure, water (60 ml) was added and the mixture was extracted with methylene chloride (3×60 ml). The combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure to give the ketone (4.08 g) as a yellow solid, m.p. 160°-165° C.

Provenance & Evidence