Methyl morpholine oxide → 5-Chloro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde

HRID 1669778Notes

Reaction equation

HRID 1669778 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12](Br)Br)=[C:8]2[C:3]=1[C:4](=[O:16])[CH:5]=[C:6]([CH3:15])[O:7]2.C[N+]1([O-])CC[O:21]CC1>C(#N)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=[O:21])=[C:8]2[C:3]=1[C:4](=[O:16])[CH:5]=[C:6]([CH3:15])[O:7]2

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 574388935-chloro-8-(dibromomethyl)-2-methyl-4H-chromen-4-one

Product 1

HCID 574388945-Chloro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

210 mg (0.57 mmol) of 5-chloro-8-(dibromomethyl)-2-methyl-4H-chromen-4-one are heated with 147 mg (1.2 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. 22 mg (17% 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-61f0625179394896a07f395e4e343a5d
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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