Methyl morpholine oxide → 8-Formyl-2-methyl-4-oxo-4H-1-benzopyran-5-carbonitrile
Reaction equation
Br[CH:2](Br)[C:3]1[C:12]2[O:11][C:10]([CH3:13])=[CH:9][C:8](=[O:14])[C:7]=2[C:6]([C:15]#[N:16])=[CH:5][CH:4]=1.C[N+]1([O-])CC[O:22]CC1>C(#N)C>[CH:2]([C:3]1[C:12]2[O:11][C:10]([CH3:13])=[CH:9][C:8](=[O:14])[C:7]=2[C:6]([C:15]#[N:16])=[CH:5][CH:4]=1)=[O:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
260 mg (0.72 mmol) of 8-(dibromomethyl)-2-methyl-4-oxo-4H-chromene-5-carbonitrile are heated with 187 mg (1.6 mmol) of N-methylmorpholine N-oxide with the addition of molecular sieves in 15 ml of acetonitrile under reflux overnight. After filtration through kieselguhr, the solvent is removed in vacuo, and the residue is purified by preparative HPLC. 23 mg (15% of theory) of the title compound are obtained.