Methyl morpholine oxide → 8-Formyl-2-methyl-4-oxo-4H-1-benzopyran-5-carbonitrile

HRID 557431Notes

Reaction equation

HRID 557431 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

HCID 82029Methyl morpholine oxideHCID 578286218-(Dibromomethyl)-2-methyl-4-oxo-4H-1-benzopyran-5-carbonitrile

Product 1

HCID 578286138-Formyl-2-methyl-4-oxo-4H-1-benzopyran-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. temperatureunder reflux overnight
  2. filtrationAfter filtration through kieselguhr
  3. customthe solvent is removed in vacuo
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-ddce7f24a8f542deb19af123e9a9deb8
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

Loading…